Dr. Friday explains why Airbnb and short-term rental owners need careful tax allocation and recordkeeping. She also notes compliance requirements at federal, state, and local levels.
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Tax questions
Real estate & rentals
Rental income, depreciation, 1031 exchanges, selling a home, and short-term rentals.
All topics
IRS letters & problems
Deadlines & filing
Deductions & credits
Small business & self-employed
Real estate & rentals
Retirement & Social Security
Family & education
Estate, gifts & inheritance
Investments & capital gains
Bookkeeping & payroll
Health & insurance
45 answers
Dr. Friday explains that meeting the 750-hour test alone does not guarantee real estate professional status. She warns that taxpayers with full-time non-real-estate jobs often face IRS disallowance.
ListenDr. Friday discusses opportunity zones as another way to defer capital gains. She notes timing rules and longer holding periods can be key to the tax outcome.
ListenDr. Friday explains standard depreciation periods for residential and commercial rentals. She also covers cost segregation benefits and why recapture should be part of long-term planning.
ListenDr. Friday reviews the core 1031 like-kind exchange rule for real estate investors. She explains how reinvesting proceeds can defer capital gains instead of paying tax immediately.
ListenDr. Friday explains the mortgage interest deduction limits and why only a portion of interest may be deductible for larger loans. She also notes that some older mortgages…
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Qualified Opportunity Zones: A Powerful Capital Gains Tool
Investments & capital gains
Have a large capital gain? Dr. Friday explains how investing through Qualified Opportunity Zones can eliminate tax and help struggling communities.
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Radio Show
October 11, 2025
With the November 3rd deadline for 2024 tax returns fast approaching, Dr. Friday is in the studio to tackle some of the most pressing tax questions. In this…
#Business Versus Hobby Losses#Rental Property Sales#Senior Tax Deduction#Estate Planning
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Radio Show
June 7, 2025
Welcome to another episode of the Dr. Friday Radio Show! In this episode Dr. Friday Show emphasizes one key theme: planning ahead! Whether you're considering selling stock, dealing…
#Capital Gains Deferral#Estimated Tax Payments#Retirement Tax Planning#Disaster Tax Extensions
ListenDr. Friday explains how a 1031 exchange allows real estate investors to defer capital gains taxes by reinvesting in a similar property.
ListenDr. Friday explains the tax differences between professional real estate investors and casual investors, highlighting the 750-hour rule.
ListenIn this episode, Dr. Friday explains the tax consequences of selling your home, including home exclusions, rental conversions, and potential deductions.
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