Capital Gains Rules When You Sell a Home and Buy Another

In this Tax Tuesday episode, Barley Bowler, CPA, and Eliot Thomas, Esq., tackle a diverse range of tax questions covering business structures, real estate investments, and tax optimization strategies. They demonstrate significant tax savings by comparing Schedule C sole proprietorship versus S Corporation structures, showing how proper business formation can save approximately $6,000 annually on just $50,000 of income. The hosts address healthcare deductions for S Corporation owners, explain the complexities of the self-employed limited partner exception, and dive deep into capital gains calculations and 1031 exchanges. They also cover tax lien investments, charitable boat donations, and probate avoidance strategies. With practical examples and real calculations, this episode provides actionable advice for entrepreneurs and real estate investors looking to minimize their tax burden while staying compliant with IRS regulations.

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Highlights/Topics:

• "What is the best way to reduce my income and my self-employment taxes? I'm single, a handyman/contractor with no dependents. I work solo, no employees." - Form S Corporation, pay reasonable wage, save on employment taxes.
• "I have an S-Corp LLC for my property management and business consulting activities. I'd like to provide my me and my spouse's healthcare through the LLC. What's the best way to go about this?" - S Corporation pays premiums, adds to W2, deducts on Schedule 1.
• "Self-employed limited partner exception. Please talk about this topic." - Very risky strategy; IRS cracking down; use S-Corporation instead.
• "How can one start a business, LLC or C-corp, and an ideal state of incorporation and hold those shares in a Roth IRA?" - Cannot own an operating business in Roth IRA; consider ROBS instead.
• "What types of taxes and tax reporting will be involved if I begin investing in tax liens?" - Interest income or property ownership; depending on the redemption outcome.
• "What are the rules for capital gains taxes on the sale of a house when the profits are used to pay cash on the next property?" - Sales price minus adjusted basis equals gain; cash use is irrelevant.
• "I am taking my primary home and turning it into a rental for one to two years. How do taxes work if you wanted to 1031 a portion of the gains?" - Take Section 121 exclusion first, then 1031 the remaining gain.
• "Under a 1031, taxpayers must select three possible real estate properties within 45 days. Can these selected properties be changed before the 180-day deadline?" - No changes allowed after 45 days; very strict timeline rules.
• "I have a boat to donate to charity. Is it true that I can make a $5,000 donation without having a certified appraiser?" - Yes, under $5,000 needs written acknowledgment, not certified appraisal.
• "What are the ways we can avoid probate?" - Living trust, joint ownership, beneficiary designations, lifetime gifting strategies

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