Charitable Gift Opportunities for Residences and Vacation Homes: Lifetime and Testamentary Strategies

Please join us for a special program, presented jointly by the Sarasota County Bar Association and Charitable Gift Planners of Southwest Florida!

Tuesday, October 20, 2026
12:00 – 1:00 p.m. 

Registration Details: 
Free for SCBA & CGPSWFL Members

Click here to register for this virtual session. (All attendees will register through the Sarasota County Bar Association website.)

Southwest Florida is home to a vibrant philanthropic community supported by many generous donors and impactful charitable organizations.  This program is designed for real property, probate and trust law attorneys, along with philanthropic fundraisers to facilitate the collaboration among professional advisors, enhance donor engagement in gift conversations and to learn the nuts and bolts of impactful ways to make charitable gifts of primary residences and vacation homes.

This program will focus primarily on lifetime gifts of a remainder interest in a residence or vacation home, sometimes referred to as a “retained life estate,” as prescribed in IRC Section 170(f)(3)(B)(i) and the corresponding Treasury Regulations. We’ll discuss in detail the legal requirements to establish the gift and how to illustrate the charitable income tax benefits and other consequences to the donor. Through case studies we will highlight ideal candidate profiles and walk through the practical mechanics of the gift of a remainder interest strategy.

In addition, we will discuss alternative methods for donors to make gifts of residences and vacation homes, via:

• Outright lifetime gifts
  
  
• Lifetime bargain sales
  
  
• Lifetime and testamentary charitable remainder trusts

About Our Speaker: David K. Cahoone, J.D., LL.M (in Taxation)

David is a Senior Partner with The Dorcey Law Firm in Southwest Florida. David is also a consultant, author, and frequent public speaker. He has over 30 years of active practice experience in the areas of wealth transfer planning, charitable planning, trusts and estates, income tax planning and business planning. David has significant experience planning with ultra-high-net-worth families and individuals and working with them in all phases of design, implementation and ongoing support.

David enjoys engaging with individuals, families and business owners to develop and implement plans to achieve their unique goals and objectives by listening to discover and then working with them to build a plan to implement, their "enlightened dreams" for themselves, their loved ones, their communities and their philanthropic passions.

David also assists public charities and private foundations with navigating the challenging requirements for accepting complex gifts and providing proper documentation to donors and IRS compliance. He also provides training to charitable fundraisers and presentations to charitable donors who are looking to be more tax efficient in their charitable giving.

David has a Masters degree in Taxation from the University of Florida College of Law and has attained the highest professional ranking (AV) from Martindale-Hubbell. He is a member of the Southwest Florida Estate Planning Counsel, National Association of Charitable Gift Planners, Charitable Gift Planners of Southwest Florida, and the Sarasota County and Florida Bar Associations (Sections on Business Law, Tax Law, Real Property and Trust Law).

David is a co-author of Protect and Enhance Your Estate published by McGraw Hill and The Living Trust Workbook published by the Penguin Group. He has been quoted in national newspapers and magazines and appeared as a guest on a number of radio talk shows. David is also a frequent keynote speaker for local and national organizations.

For five years David was the Director of Philanthropic Strategies and Planned Giving at Brown University. At Brown he worked collaboratively with the Advancement office, faculty, staff and alumni as a resource for donors and their advisors to develop and achieve their charitable and financial goals and dreams in a tax-wise manner.

David looks forward to working collaboratively with other attorneys, fundraising professionals, CPAs, financial advisors, and insurance professionals to serve the specialized planning needs of high-net-worth individuals, families and business owners.