Tax questions
Stocks, crypto, capital gains and losses, wash sales, and dividend and interest income.
This episode stays focused on last-minute tax-season decisions, especially for Tennessee listeners affected by the IRS winter storm extension to May 22, 2026. Dr. Friday explains why filing…
#IRS Debt Resolution#Estimated Tax Payments#Disaster Tax Extensions#IRS Notice Resolution
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 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 discusses step-up in basis and why timing of transfers can affect taxes. She notes that gifting during life can sometimes leave tax savings on the table.
ListenDr. Friday takes live calls focused on practical tax decisions people are facing right now. She explains how capital gains work on inherited and sold property, why basis…
#Senior Tax Deduction#Inherited Property Basis#Business Vehicle Deductions#Tax Preparer Accountability
ListenDr. Friday explains why inherited property can receive a step-up in basis, which may reduce future taxes. She cautions that quitclaiming property to children early can be a…
ListenDr. Friday highlights areas the IRS tends to prioritize for enforcement, including higher-income taxpayers and complex pass-through entities. She also notes increased attention on digital assets and offshore…
ListenDr. Friday explains a new IRS form, 1099-DA, that begins in 2025 for digital assets. She notes it will work much like a 1099-B and makes it easier…
ListenDr. Friday explains that long-term capital gains rates still generally fall into the 0%, 15%, and 20% brackets. She also reminds higher earners to factor in the 3.8%…
ListenOne-minute answer
Investments & capital gains
Have a large capital gain? Dr. Friday explains how investing through Qualified Opportunity Zones can eliminate tax and help struggling communities.
ListenDr. Friday highlights a little-known opportunity for investors who hold qualified small business stock for five years or more—potentially eliminating capital gains tax.
ListenWelcome to another episode of the Dr. Friday Radio Show. In this episode, Dr. Friday gets into pressing tax topics, including a potential new bill affecting overtime and…
#IRS Debt Resolution#Overtime And Tip Deductions#Home Sale Exclusion#Inherited Property Basis
ListenAsk Dr. Friday
Send it in. Questions may be answered on an upcoming episode or video, first name only.
