Episode 45: Family Travel Fairness, STR Bonus Depreciation, and Digital Risk Management

February 23rd, 2026  |  37 mins 26 secs

asset protection, bonus depreciation, charitable giving, cybersecurity, family dynamics, financial literacy, gifting strategies, intergenerational wealth, real estate investing, short-term rentals, tax planning, vacation rental

In this episode, we explore how complexity shows up in family dynamics, tax strategy, and digital risk. We discuss how parents can navigate lifestyle differences among adult children without falling into the reallocation trap, unpack how bonus depreciation for short-term rentals actually works under the One Big Beautiful Bill, and close with a From the Field conversation on modern cybersecurity risks facing high-profile families and family offices.