Can I Take A Loss On My Rental Property If I Sell It?

Today, attorneys Toby Mathis, Esq., and Eliot Thomas, Esq., delve into listener questions including - how gains from crypto investments are classified as either ordinary income or capital gains. For property sales, we explore strategies to avoid capital gains tax, such as donating to a private foundation, and we clarify the impact of marriage timing on capital gains claims. We also cover tax implications for rental property expenses, including the timing of write-offs for losses and the criteria for short-term rental deductions. Additionally, we touch on medical reimbursements for C-corps, renovations for Airbnb setups, and backdoor Roth IRAs.
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Highlights/Topics:

• "What are the basic principles to keep in mind with gains derived from investing in crypto?" - gains from a “personal asset” need to be identified as ordinary income or capital gains
• "Is there a legal way to sell a property through a charity to avoid a capital gain and have the charity provide us with a small monthly retirement amount?" - If you already have a private foundation, you could still do this transaction as long as you gave the property to the private foundation.
• "My fiance and I purchased a property together. He is selling his property that he has owned for over 10 years. We are not married yet, but intend to get married this year. If we get married after he sells his property, can we still claim status for capital gains? He will have a significant amount of capital gains on his property. His property will sell in August, and we weren’t going to get married till October. We just want to make sure we’re okay to claim status for capital gains." - I think what we're getting at here is the 121 exclusion, if you meet the criteria.
• "I purchased a duplex and we’ll list it as a short-term rental in August." I want to buy furniture and supplies and do both major and minor repairs before the listing is active. Can I write off these expenses before the Airbnb listing is active?" - Generally speaking, no, you're not going to write it off before it's active.
• "I bought an investment property for $260,000. It’s only worth $200,000. If I sell it, can I take a $60,000 loss?" - If we bought it as investment, maybe it was a flip or something like that, we can take it as an ordinary loss.
• "For short-term qualification, do we need to add it to Airbnb or Vrbo, or can we just rent it out to friends and family for three rentals of less than a week and still qualify for the deduction?" If yes, how do we show proof?” - there's no requirement that you specifically set up an Airbnb or VRBO, but you can’t rent to friends and family or “related parties” - that’s personal use.
• "Can you reimburse medical costs if organized as a C-corp?" - Simple answer, yes, if you have a medical reimbursement plan.
• "Can I make renovations to my personal residence to establish an Airbnb and write off the costs?" - yes you can, depreciated over time. It must be in service to deduct.
• "What is a backdoor Roth?" - You can put it in the Roth after you pay taxes on it, if you make an income over the typical limit for Roth contributions.
• "What is a good way to plan when converting a primary residence into a rental property and have a tax-wise setup for the transition? Do we sell the property to the LLC or transfer sign the loan to the LLC? How will the capital gains be treated?" - you could do either one.

Resources:

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