[sheet: Closing Checklist]
Item No. | Category | Description | Responsible Party | Due Date | Status | Notes
I-1 | I. Trust Formation | Trust Agreement — The Salvatore A. Pellegrino 2025 Family Trust: Irrevocable trust instrument executed by Salvatore A. Pellegrino (Grantor) and Cornerstone Fiduciary Services, Inc. (Helena R. Matsuda, Senior Trust Officer) as Independent Trustee; incorporates grantor-trust defect provisions under IRC § 675(4)(C); names beneficiaries Marco A. Pellegrino, Lucia Pellegrino-Vasquez, Dante R. Pellegrino, and their descendants; governed by Florida law | Calderwood & Harkness LLP (Rafael Dominguez / Leonard Cross); Cornerstone Fiduciary Services, Inc.; Ridgeway & Callahan LLP (Patricia N. Callahan) | 2025-11-10 | Executed | Executed November 10, 2025. Cornerstone FL Trust Co. License No. FTC-2014-00287 confirmed.
I-2 | I. Trust Formation | Seed Gift Assignment Agreement: Irrevocable gift of $2,000,000 in cash from Salvatore A. Pellegrino to the 2025 IDGT as initial trust corpus; utilizes $2,000,000 of Grantor's remaining federal gift-tax exemption (remaining exemption pre-seed: $7,850,000; post-seed: $5,850,000) | Calderwood & Harkness LLP (Rafael Dominguez); Salvatore A. Pellegrino; Cornerstone Fiduciary Services, Inc. | 2025-11-10 | Executed | Executed November 10, 2025. Wire to Prescott National Bank trust account per wire instructions.
I-3 | I. Trust Formation | Cornerstone Fiduciary Services, Inc. — Acceptance of Trusteeship: Written acceptance by Helena R. Matsuda, Senior Trust Officer, on behalf of Cornerstone | Cornerstone Fiduciary Services, Inc. | 2025-11-10 | Executed | Received with executed Trust Agreement.
I-4 | I. Trust Formation | Trust Tax ID Application (IRS Form SS-4): Application for EIN for The Salvatore A. Pellegrino 2025 Family Trust | Baxter Whitfield CPA Group, P.A. (Sandra T. Whitfield) | 2025-11-10 | Pending | Application filed; EIN pending issuance by IRS.
I-5 | I. Trust Formation | Crummey Withdrawal Notice Letters: Notices to each current beneficiary (Marco A. Pellegrino, Lucia Pellegrino-Vasquez, Dante R. Pellegrino) of right to withdraw pro rata share of seed gift for 30-day withdrawal period | Calderwood & Harkness LLP (Rafael Dominguez); Cornerstone Fiduciary Services, Inc. | 2025-11-10 | Executed | Notices mailed November 10, 2025. Withdrawal period expired December 10, 2025; no withdrawals exercised.
II-1 | II. Transaction Documents | Membership Interest Purchase Agreement (MIPA): Sale of membership interests in Meridian Shores Hospitality LLC (92% Class A, post-discount value $17,920,000), Costa Luma Resort Holdings LLC (100%, post-discount value $14,800,000), and Azulia Beach Club LLC (88% Class A, post-discount value $7,280,000) from Salvatore A. Pellegrino (acting through PCG) to the 2025 IDGT. Aggregate purchase price: $40,000,000, payable via secured promissory note. Supported by qualified appraisal by Hargrove & Lindquist LLP applying 20% combined DLOM/DLOC discount to aggregate gross FMV of $50,000,000. | Calderwood & Harkness LLP (Rafael Dominguez / Cynthia Ho); Ridgeway & Callahan LLP (Patricia N. Callahan) | 2025-12-15 | Draft Circulated | Draft circulated November 17, 2025. Final trustee-counsel comments due December 1, 2025.
II-2 | II. Transaction Documents | Secured Promissory Note ($40,000,000): Issued by Cornerstone Fiduciary Services, Inc. as Trustee of the 2025 IDGT (Maker) in favor of Salvatore A. Pellegrino (Payee). Principal: $40,000,000; Interest: 4.40% per annum (September 2025 mid-term AFR, annual compounding); Term: 9 years maturing December 15, 2034; Annual interest-only payments of $1,760,000; Balloon principal at maturity. | Calderwood & Harkness LLP (Rafael Dominguez / Leonard Cross); Ridgeway & Callahan LLP | 2025-12-15 | Draft Circulated | Draft circulated November 17, 2025.
II-3 | II. Transaction Documents | Pledge and Security Agreement: First-priority security interest granted by the 2025 IDGT (Pledgor) to Salvatore A. Pellegrino (Secured Party) in all membership interests in Meridian Shores Hospitality LLC, Costa Luma Resort Holdings LLC, and Azulia Beach Club LLC, plus all distributions, proceeds, and cash flow attributable thereto. Secures obligations under the $40,000,000 Secured Promissory Note. | Calderwood & Harkness LLP (Rafael Dominguez / Cynthia Ho) | 2025-12-15 | Draft Circulated | Draft circulated November 17, 2025. Includes UCC financing statement authorization.
II-4 | II. Transaction Documents | Assignment of Membership Interests — Meridian Shores Hospitality LLC: Short-form assignment of 92% Class A membership interest from Salvatore A. Pellegrino / PCG (Assignor) to the 2025 IDGT (Assignee). EIN: 59-4021867. Property: 4500 Gulf Shore Boulevard, Naples, FL 34102. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | To be executed at closing.
II-5 | II. Transaction Documents | Assignment of Membership Interests — Costa Luma Resort Holdings LLC: Short-form assignment of 100% membership interest. EIN: 59-4173920. Property: 81700 Overseas Highway, Islamorada, FL 33036. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | To be executed at closing.
II-6 | II. Transaction Documents | Assignment of Membership Interests — Azulia Beach Club LLC: Short-form assignment of 88% Class A membership interest. EIN: 59-4285413. Property: 22 Baymont Drive, Clearwater Beach, FL 33767. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | To be executed at closing.
II-7 | II. Transaction Documents | Amended and Restated Operating Agreement — Meridian Shores Hospitality LLC: Reflects admission of the 2025 IDGT (Cornerstone as Trustee) as holder of 92% Class A membership interest; addresses trustee voting rights, distribution waterfall, transfer restrictions consistent with Pledge and Security Agreement; Marco A. Pellegrino continues as COO. | Calderwood & Harkness LLP (Rafael Dominguez) | 2025-12-15 | In Preparation | To be executed at closing. Estimated annual distributable cash flow across portfolio: $4,800,000 (coverage ratio 2.73×).
II-8 | II. Transaction Documents | Amended and Restated Operating Agreement — Costa Luma Resort Holdings LLC: Reflects admission of the 2025 IDGT as holder of 100% membership interest; addresses trustee management rights and distribution provisions. | Calderwood & Harkness LLP (Rafael Dominguez) | 2025-12-15 | In Preparation | To be executed at closing.
II-9 | II. Transaction Documents | Amended and Restated Operating Agreement — Azulia Beach Club LLC: Reflects admission of the 2025 IDGT as holder of 88% Class A membership interest; addresses trustee voting rights and distribution provisions. | Calderwood & Harkness LLP (Rafael Dominguez) | 2025-12-15 | In Preparation | To be executed at closing.
III-1 | III. Ancillary Deliverables | UCC-1 Financing Statement — Meridian Shores Hospitality LLC: Filed with FL Secretary of State to perfect security interest in membership interests. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | To be filed at or promptly after closing.
III-2 | III. Ancillary Deliverables | UCC-1 Financing Statement — Costa Luma Resort Holdings LLC: Filed with FL Secretary of State. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | To be filed at or promptly after closing.
III-3 | III. Ancillary Deliverables | UCC-1 Financing Statement — Azulia Beach Club LLC: Filed with FL Secretary of State. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | To be filed at or promptly after closing.
III-4 | III. Ancillary Deliverables | Consent of Existing Members — Meridian Shores Hospitality LLC: Written consent of remaining 8% members (if required under existing operating agreement) to transfer of 92% Class A interest to the Trust. | Calderwood & Harkness LLP (Cynthia Ho); Pellegrino Capital Group LLC | 2025-12-15 | In Progress | Consent forms distributed; awaiting signatures.
III-5 | III. Ancillary Deliverables | Consent of Existing Members — Azulia Beach Club LLC: Written consent of remaining 12% members (if required) to transfer of 88% Class A interest to the Trust. | Calderwood & Harkness LLP (Cynthia Ho); Pellegrino Capital Group LLC | 2025-12-15 | In Progress | Consent forms distributed; awaiting signatures.
III-6 | III. Ancillary Deliverables | Officer/Manager Certificate — Pellegrino Capital Group LLC: Certificate of Salvatore A. Pellegrino as Managing Member of PCG (EIN 65-1238074) confirming authority to execute transaction documents, incumbency, and formation in good standing (organized 2006, FL). | Salvatore A. Pellegrino; Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Preparation | Draft to be prepared.
III-7 | III. Ancillary Deliverables | Officer Certificate — Cornerstone Fiduciary Services, Inc.: Certificate confirming Helena R. Matsuda's authority to execute documents on behalf of the Trustee. | Cornerstone Fiduciary Services, Inc. (Helena R. Matsuda) | 2025-12-15 | Requested | Request sent to Cornerstone.
III-8 | III. Ancillary Deliverables | Good Standing Certificates — Meridian Shores Hospitality LLC, Costa Luma Resort Holdings LLC, Azulia Beach Club LLC, and PCG: Current certificates from FL Secretary of State. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-15 | In Progress | Orders placed with FL Secretary of State.
III-9 | III. Ancillary Deliverables | Legal Opinion — Calderwood & Harkness LLP: Opinion letter to Cornerstone Fiduciary Services, Inc. regarding enforceability of MIPA, promissory note, and pledge agreement; arm's-length nature of the transaction. | Calderwood & Harkness LLP (George Trujillo / Leonard Cross) | 2025-12-15 | In Preparation | Draft in progress.
III-10 | III. Ancillary Deliverables | Letter to Cornerstone Fiduciary Services — Transaction Summary and Appraisal Confirmation: Letter from George Trujillo and Leonard Cross to Helena R. Matsuda (cc: Patricia N. Callahan, Ridgeway & Callahan LLP) summarizing transaction, confirming appraisal support, enclosing draft MIPA, note, and pledge agreement. | Calderwood & Harkness LLP (George Trujillo / Leonard Cross) | 2025-11-17 | Sent | Sent November 17, 2025. Comments requested by December 1, 2025.
IV-1 | IV. Appraisal and Valuation | Qualified Appraisal Report — Hargrove & Lindquist LLP: Independent business valuation of membership interests in Meridian Shores Hospitality LLC (pre-discount FMV $22,400,000; 2024 NOI $3,200,000; 7.0× multiple), Costa Luma Resort Holdings LLC (pre-discount FMV $18,500,000; 2024 NOI $2,640,000; 7.0× multiple), and Azulia Beach Club LLC (pre-discount FMV $9,100,000; 2024 NOI $1,300,000; 7.0× multiple). Aggregate gross FMV: $50,000,000. 20% combined DLOM/DLOC discount applied uniformly. Aggregate discounted FMV: $40,000,000. Prepared by Dennis W. Hargrove, ASA, CFA, Managing Director. | Hargrove & Lindquist LLP (Dennis W. Hargrove) | 2025-11-03 | Received | Report delivered November 3, 2025. Valuation engagement letter signed October 6, 2025. Address: 3344 Peachtree Road NE, Suite 900, Atlanta, GA 30326.
IV-2 | IV. Appraisal and Valuation | Appraiser Independence Confirmation: Written confirmation from Hargrove & Lindquist LLP of appraiser independence and qualifications under IRS qualified appraisal standards. | Hargrove & Lindquist LLP (Dennis W. Hargrove) | 2025-11-03 | Received | Included with appraisal report.
V-1 | V. Banking and Funds Flow | Prescott National Bank — Trust Account Opening: Opening of depository account for The Salvatore A. Pellegrino 2025 Family Trust at Prescott National Bank (401 East Las Olas Boulevard, Fort Lauderdale, FL 33301). Contact: Thomas J. Andersen, SVP, Private Banking. | Cornerstone Fiduciary Services, Inc.; Prescott National Bank (Thomas J. Andersen) | 2025-11-10 | Complete | Account opened in connection with seed gift funding.
V-2 | V. Banking and Funds Flow | Wire Instructions — Prescott National Bank: Wire transfer instructions for the Trust's depository account for receipt of seed gift and future entity distributions. | Prescott National Bank (Thomas J. Andersen) | 2025-11-10 | Received | Wire instructions received and confirmed.
V-3 | V. Banking and Funds Flow | Seed Gift Wire Confirmation: Confirmation of $2,000,000 wire transfer from Salvatore A. Pellegrino to the 2025 IDGT trust account at Prescott National Bank. | Prescott National Bank (Thomas J. Andersen); Baxter Whitfield CPA Group, P.A. (Sandra T. Whitfield) | 2025-11-10 | Complete | Wire confirmed November 10, 2025.
V-4 | V. Banking and Funds Flow | Funds Flow Memorandum — Closing: Summary of closing funds flow for December 15, 2025 (no cash changes hands at closing; sale is via promissory note; entity distributions to flow to trust account going forward). | Calderwood & Harkness LLP (Rafael Dominguez) | 2025-12-15 | In Preparation | Draft to be circulated prior to closing.
VI-1 | VI. Post-Closing | Form 709 (United States Gift Tax Return) — 2025: Reporting $2,000,000 seed gift on Salvatore A. Pellegrino's 2025 gift tax return. 2025 applicable exclusion: $13,990,000; prior usage: $6,140,000; remaining pre-seed: $7,850,000; post-seed remaining: $5,850,000. SSN last four: 8217. | Baxter Whitfield CPA Group, P.A. (Sandra T. Whitfield); Calderwood & Harkness LLP (Leonard Cross) | 2026-04-15 | Not Yet Due | Filing deadline April 15, 2026. Sale at discounted FMV is not a gift (arm's-length sale supported by qualified appraisal); no gift-tax reporting for sale.
VI-2 | VI. Post-Closing | Record Copies — Executed Transaction Documents: Assemble and distribute record copies of all executed closing documents to PCG, Cornerstone, Ridgeway & Callahan, Baxter Whitfield, and Prescott National Bank. | Calderwood & Harkness LLP (Cynthia Ho) | 2025-12-31 | Not Yet Due | To be compiled after closing.
VI-3 | VI. Post-Closing | UCC Filing Confirmations: Confirm receipt of filed and stamped UCC-1 financing statements from FL Secretary of State for all three entities. | Calderwood & Harkness LLP (Cynthia Ho) | 2026-01-15 | Not Yet Due | Monitor for filing confirmations post-closing.
VI-4 | VI. Post-Closing | Entity Record Updates — Membership Ledgers: Update internal membership ledgers and capital account records for Meridian Shores Hospitality LLC, Costa Luma Resort Holdings LLC, and Azulia Beach Club LLC to reflect the Trust as new member. | Pellegrino Capital Group LLC (Dante R. Pellegrino); Baxter Whitfield CPA Group, P.A. | 2025-12-31 | Not Yet Due | To be completed post-closing.
VI-5 | VI. Post-Closing | Promissory Note Payment Schedule: Confirm first annual interest payment date and establish payment calendar ($1,760,000 annually through December 15, 2034; $40,000,000 balloon at maturity). | Cornerstone Fiduciary Services, Inc. (Helena R. Matsuda); Prescott National Bank | 2025-12-31 | Not Yet Due | First interest payment due December 15, 2026.
VI-6 | VI. Post-Closing | Matter File Close-Out and Archival: Close Calderwood & Harkness matter file 1027-00005 / billing code 78500.00014 upon completion of all post-closing items. | Calderwood & Harkness LLP (Rafael Dominguez) | 2026-05-01 | Not Yet Due | Target close-out after Form 709 filing.
[sheet: Summary]
Field | Detail
Matter Name | Pellegrino Capital Group LLC — Intra-Family Wealth Transfer via Sale to Defective Grantor Trust
Matter Number | 1027-00005
Billing Code | 78500.00014
Client | Pellegrino Capital Group LLC (EIN 65-1238074), 2400 Salzedo Street, Suite 1200, Coral Gables, FL 33134
Grantor | Salvatore A. Pellegrino
Grantor Residence | 610 Casuarina Concourse, Coral Gables, FL 33143
Trust | The Salvatore A. Pellegrino 2025 Family Trust (2025 IDGT)
Independent Trustee | Cornerstone Fiduciary Services, Inc. (Helena R. Matsuda, Senior Trust Officer), 200 West Forsyth Street, Suite 1500, Jacksonville, FL 32202; FL Trust Co. License No. FTC-2014-00287
Trustee's Counsel | Ridgeway & Callahan LLP (Patricia N. Callahan, Partner), 50 North Laura Street, Suite 2200, Jacksonville, FL 32202
Beneficiaries | Marco A. Pellegrino (1285 Gulf Pavilion Drive, Naples, FL 34108); Lucia Pellegrino-Vasquez (3300 Brickell Avenue, Unit 4402, Miami, FL 33129); Dante R. Pellegrino (807 Harbour Post Drive, Tampa, FL 33602); and their descendants
Grantor's Spouse | Adriana M. Pellegrino, 610 Casuarina Concourse, Coral Gables, FL 33143
Valuation Firm | Hargrove & Lindquist LLP (Dennis W. Hargrove, ASA, CFA, Managing Director), 3344 Peachtree Road NE, Suite 900, Atlanta, GA 30326
Family Accountants | Baxter Whitfield CPA Group, P.A. (Sandra T. Whitfield, CPA, Managing Partner), 150 Alhambra Circle, Suite 800, Coral Gables, FL 33134
Depository Bank | Prescott National Bank (Thomas J. Andersen, SVP, Private Banking), 401 East Las Olas Boulevard, Fort Lauderdale, FL 33301
Engagement Counsel | Calderwood & Harkness LLP, 701 Brickell Avenue, Suite 3100, Miami, FL 33131 (Miami Office); HQ: 1345 Avenue of the Americas, New York, NY 10105
C&H Team — Responsible Partner | George Trujillo
C&H Team — Billing Partner | Kevin Ostrowski
C&H Team — Lead Associate | Rafael Dominguez
C&H Team — Working Associate | Cynthia Ho
C&H Team — Tax Specialist Partner | Leonard Cross
Checklist Prepared By | Rafael Dominguez and Cynthia Ho
Target Closing Date | December 15, 2025
Transaction Summary | Sale of membership interests in Meridian Shores Hospitality LLC, Costa Luma Resort Holdings LLC, and Azulia Beach Club LLC to the 2025 IDGT for $40,000,000 (aggregate discounted FMV after 20% combined DLOM/DLOC discount on $50,000,000 aggregate gross FMV), payable via $40,000,000 secured promissory note at 4.40% (Sept. 2025 mid-term AFR). Seed gift of $2,000,000 funded November 10, 2025.
Governing Law | State of Florida
Grantor Trust Provisions | IRC §§ 671–679; defective under § 675(4)(C) (power to substitute assets of equivalent value)
[sheet: Key Dates]
Date | Event | Status
2025-09-18 | Matter opened; engagement letter executed by PCG and Calderwood & Harkness LLP | Complete
2025-09-25 | Planning memorandum circulated (Leonard Cross to Salvatore A. Pellegrino) | Complete
2025-10-06 | Valuation engagement letter signed with Hargrove & Lindquist LLP | Complete
2025-10-20 | Draft trust instrument circulated to Cornerstone Fiduciary Services / Ridgeway & Callahan LLP | Complete
2025-11-03 | Appraisal report delivered by Hargrove & Lindquist LLP | Complete
2025-11-10 | Trust Agreement executed; seed gift of $2,000,000 funded | Complete
2025-11-17 | Draft MIPA and Secured Promissory Note circulated | Complete
2025-12-01 | Final comments from trustee's counsel (Ridgeway & Callahan LLP) due | Pending
2025-12-15 | Target closing — sale of membership interests to 2025 IDGT; promissory note issued; pledge and security agreement executed; assignments delivered | Pending
2026-04-15 | Form 709 filing deadline (2025 gift tax return for Salvatore A. Pellegrino) | Not Yet Due
2034-12-15 | Promissory note maturity — $40,000,000 balloon principal payment due | Not Yet Due
[sheet: Entity & Valuation Summary]
Entity | EIN | Entity Type | Jurisdiction | Property Address | Salvatore's Interest | 2024 NOI | Valuation Multiple | Pre-discount FMV | Combined DLOM/DLOC discount | Discount Amount | Post-discount FMV
Meridian Shores Hospitality LLC | 59-4021867 | FL LLC | Florida | 4500 Gulf Shore Boulevard, Naples, FL 34102 | 92% Class A | $3,200,000 | 7.0 | $22,400,000 | 20% | $4,480,000 | $17,920,000
Costa Luma Resort Holdings LLC | 59-4173920 | FL LLC | Florida | 81700 Overseas Highway, Islamorada, FL 33036 | 100% | $2,640,000 | 7.0 | $18,500,000 | 20% | $3,700,000 | $14,800,000
Azulia Beach Club LLC | 59-4285413 | FL LLC | Florida | 22 Baymont Drive, Clearwater Beach, FL 33767 | 88% Class A | $1,300,000 | 7.0 | $9,100,000 | 20% | $1,820,000 | $7,280,000
TOTAL | $7,140,000 | $50,000,000 | 20% | $10,000,000 | $40,000,000
[sheet: Note & Exemption Summary]
Item | Value
Promissory Note Principal | $40,000,000
Interest Rate (Sept. 2025 Mid-Term AFR) | 4.40% per annum (annual compounding)
Note Term | 9 years (December 15, 2025 – December 15, 2034)
Annual Interest-Only Payment | $1,760,000 ($40M × 4.40%)
Balloon Principal at Maturity | $40,000,000
Seed Gift (Cash) | $2,000,000 (5% of sale price)
Note-to-Seed Ratio | 10:1 ($40M note / $4M total trust equity including seed and projected Year-1 cash flow)
Estimated Annual Distributable Cash Flow | $4,800,000 (12% cash-on-cash yield on $40M)
Debt Service Coverage Ratio | 2.73× ($4,800,000 / $1,760,000)
2025 Federal Applicable Exclusion Amount | $13,990,000
Prior Exemption Usage | $6,140,000
Remaining Exemption (Pre-Seed) | $7,850,000 ($13,990,000 − $6,140,000)
Remaining Exemption (Post-Seed) | $5,850,000 ($7,850,000 − $2,000,000)
Salvatore's Estimated Gross Estate | ~$285,000,000
PCG Total AUM | ~$215,000,000
Security for Note | First-priority pledge of acquired membership interests plus assignment of distributions