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Something nobody has mentioned yet - have you considered a Delaware Statutory Trust (DST) investment? It's technically still real estate so you can use a 1031 exchange, but you become a passive investor without landlord responsibilities. Might be a middle ground if you want out of active property management but still want the tax benefits of a 1031.
That's an interesting option I hadn't considered. How does the income work from something like that? Is it comparable to what you might get from a rental property? And would I still qualify if I'm coming from a partnership LLC structure?
The income from a DST is typically distributed monthly or quarterly and is generally comparable to what you might see from a rental property, usually in the 4-6% range depending on the specific trust. Many DSTs focus on stable, long-term leased properties like corporate office buildings or industrial spaces. Yes, you would still qualify coming from a partnership LLC structure, though there are some complexities to navigate. Each partner in your LLC would need to be treated as an individual investor in the 1031 exchange process. You would likely need to either dissolve the partnership before the exchange or have the partnership itself invest in the DST, depending on your specific situation and goals.
Have you talked to your partner about possibly not selling at all? If you refinance the property instead of selling it, you can pull cash out without triggering a taxable event. You could use that cash for your business purchase while maintaining the real estate investment.
This is actually smart advice. I did something similar last year. Refinanced my rental property at 4.5% and used the cash to buy into a local business. The interest is deductible as a business expense too if you structure it right.
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I dealt with this exact situation recently. Make sure you file Form 8606 for BOTH tax years - one for 2020 (to report the nondeductible contribution) and one for 2021 (to report the Roth conversion). The 2020 form establishes your basis of $6,000, and the 2021 form reports the conversion and calculates the taxable amount. Since your rollover IRA existed when you did the conversion, you'll need to use the pro-rata formula to determine how much is taxable. Pro-rata formula: (Nondeductible contributions ÷ Total IRA balance) × Amount converted = Nontaxable portion For example, if your total IRA balance (including the rollover IRA) was $46,000 when you converted $6,000, then: $6,000 ÷ $46,000 × $6,000 = $782.61 would be the nontaxable portion, and the rest would be taxable.
But wait, wouldn't the timing matter here? If they did the conversion before rolling over the 401k, then the pro-rata rule might not apply since there was only after-tax money in the IRA system at conversion time, right?
You're absolutely right, the timing is crucial. I missed that detail. If the Roth conversion happened before the 401k rollover, then there would only be the $6,000 nondeductible contribution in the IRA system at that time. In that case, the entire conversion would likely be nontaxable. The pro-rata rule looks at all IRA balances as of December 31 of the year of conversion, but there's an exception for funds that weren't in the IRA system at the time of conversion. If the 401k rollover happened after the conversion, the rollover wouldn't affect the taxability of the conversion.
Has anyone else had problems with FreeTaxUSA calculating Form 8606 correctly? Last year it kept showing my conversion as fully taxable even though I had basis in my traditional IRA.
I had issues with it too. You need to make sure you enter your "basis" from prior years correctly. There's a specific screen where you enter the total nondeductible contributions you've made in previous years. If you skip that or enter zero, it assumes everything is taxable.
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Consider doing a 1031 exchange if you're interested in owning other real estate! You can defer paying capital gains tax if you reinvest the proceeds into a "like-kind" property. You'd need to identify the new property within 45 days of selling and complete the purchase within 180 days, but it could save you a lot in taxes.
My brother tried to do a 1031 exchange last year and it was a complete nightmare with all the timing restrictions. Make sure you have a qualified intermediary lined up BEFORE you sell if you go this route!
Is no one going to mention that $87,000 for 35 acres that was supposedly "worthless" sounds suspiciously low if a mining company is interested? You might want to get your own appraisal or consult with a lawyer before accepting their first offer. Mining companies typically don't make offers unless they know something valuable is there.
THIS! My cousin sold some "worthless" land in Wyoming to a mining company for what seemed like a great price, only to find out later they discovered a major lithium deposit. Do your homework before selling!
Oh wow, I hadn't even thought about that! I was just excited about getting money for land I thought was worthless. Maybe I should look into what exactly they're mining for and get a second opinion on the value. Thanks for bringing this up - definitely don't want to get taken advantage of!
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Another thing to consider is that the exchange might have sent the 1099 to the IRS already. If you don't file and report those transactions, you might get a letter from the IRS later asking why the info they have doesn't match what you reported. It's much better to file correctly now than deal with notices later!
Does anyone know which type of 1099 form exchanges typically send? Is it 1099-K, 1099-MISC, or the newer 1099-B? I got something from Coinbase but I'm not sure which one it is and if it matters.
Most cryptocurrency exchanges issue either a 1099-B or 1099-K. The 1099-B is more common now and includes details about your specific transactions. The 1099-K is generally issued if you had a large volume of transactions or if you conducted certain types of crypto activities. You can tell which form you received by looking at the top right corner of the document. The form type should be clearly marked. And yes, it does matter which form you received because they report different types of information and may need to be handled differently on your tax return.
Does anyone know if free tax filing services like FreeTaxUSA can handle crypto transactions? Or do I need to pay for the premium versions of TurboTax or H&R Block? I'm trying not to spend a ton of money filing taxes for a small loss.
FreeTaxUSA can handle crypto! I used it last year for my bitcoin and ethereum trades. You just manually enter your transactions on the capital gains section. It's not as automated as the paid services but it works fine if you don't have tons of transactions.
Camila Jordan
$600 is definitely on the higher side. I'd recommend shopping around a bit. H&R Block quoted me $350 for a similar situation (multi-state, 3 W-2s, and some investment stuff). Just make sure whoever you go with is experienced with multi-state returns and early withdrawals from retirement accounts.
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Lucas Bey
•Thanks for the suggestion! Did H&R Block handle your multi-state situation well? I've heard mixed things about them for more complicated situations.
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Camila Jordan
•They did okay with my multi-state stuff, but I had to be really proactive and double-check their work. The person I got was relatively new and missed allocating some of my income correctly between states at first. After I pointed it out, they fixed it, but it made me wonder what else might have been missed if I hadn't been paying attention. If you go with H&R Block or similar, try to get their more experienced preparers and ask specifically about their experience with multi-state returns and early retirement withdrawals. The quality really varies depending on which preparer you get assigned to.
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Tyler Lefleur
Former tax preparer here! To give you a different perspective - yes, $600 is within the normal range for your situation. The multi-state issue alone typically adds $150-200 to the base price at many firms, and early IRA withdrawals add complexity because we have to determine if any exceptions apply to reduce the penalty. Four W-2s isn't a big deal by itself, but combined with everything else, your return requires significantly more time than an average one.
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Madeline Blaze
•Is there anything the OP could do to reduce the cost? Maybe organizing documents in a specific way or doing some of the prep work themselves?
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