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I'm curious about the LLC structure you mentioned. Are you putting both your owned properties and management business in the same LLC? My tax guy advised me to separate them - one LLC for properties I own and a different one for property management. Said it helps with liability protection and potentially some tax benefits.
That's a really good question! I've actually been wondering about that too. My initial plan was to have everything under one LLC for simplicity, but now I'm second-guessing if that's the best approach. Did your tax person explain any specific benefits to having them separate?
The main reason he gave was liability protection. If someone sues your property management business, they could potentially go after your personally owned properties if they're in the same LLC. With separate LLCs, there's a stronger legal separation. From a tax perspective, he mentioned it can be cleaner for accounting and if you ever want to sell either business. Also said it might give more flexibility with how you handle certain deductions and expenses. The downside is more paperwork and potentially higher costs for maintaining multiple LLCs depending on your state.
Don't forget you might need to register for a business license in your city/county and possibly get properly licensed as a property manager depending on your state laws. Some states require specific licensing for anyone collecting rent on behalf of others, even if it's just for friends. The tax stuff is important but make sure you're legally allowed to do the management work first!
This is super important! I learned this the hard way in California. Was managing just two properties for family members and got hit with a fine because I didn't have the required real estate license. Rules vary by state but better to check before you get too far along.
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One thing to consider is bank statement loans (sometimes called alternative documentation loans). I'm a mortgage broker and we use these for self-employed clients who show low income on tax returns due to deductions. Instead of using your tax returns to verify income, these loans use 12-24 months of bank statements to calculate your average monthly deposits. They're typically 0.5-1% higher interest rate than conventional loans, but they're specifically designed for business owners who write off a lot of expenses. Not all lenders offer them, but they're becoming more common. Might be worth asking about if you're still struggling to qualify with traditional documentation.
This is really interesting, I hadn't heard of this option. Do these loans work for HELOCs too, or just for primary mortgages? And any idea which lenders typically offer them? My credit score is excellent (820+), it's just this stupid DTI issue because of the deductions.
They work primarily for primary and investment property mortgages, but some lenders have started offering HELOCs with bank statement options too. It's less common for HELOCs but definitely exists. Most non-bank lenders offer some version of these programs. Companies like NewRez, Angel Oak, and North American Savings Bank are known for their bank statement loan programs. Credit unions sometimes offer them too. With your excellent credit score, you'd likely qualify for the best rates they offer on these products. I'd recommend talking to a mortgage broker rather than going directly to lenders - brokers will know which specific lenders have programs that fit your situation.
Just to add another perspective - I'm also self-employed and dealt with this exact issue. What worked for me was adding a co-borrower (my spouse) to the loan application. Even though they had lower income, having W-2 income on the application helped balance out the DTI calculations. If that's not an option, look into lenders that offer manual underwriting rather than just running your numbers through an automated system. Local credit unions and smaller banks are often more flexible with self-employed borrowers because they actually look at your entire financial situation, not just the numbers on your tax return.
Second this! Manual underwriting is the way to go for self-employed people. When we bought our house, we got denied by three big banks before finding a local credit union that actually took the time to understand my business income. They looked at my profit/loss statements and business bank accounts instead of just my tax returns.
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One important thing nobody's mentioned yet: the 2-year holding period matters for Section 1231 treatment. Since you've held the property as a rental for exactly 2 years, you're right at the line for getting ordinary loss treatment. If it was less than 2 years, your loss would be a Section 1231 loss that's treated as ordinary under the "non-recaptured net Section 1231 losses" rules from the past 5 years. Also, be very careful with your documentation of that $470k valuation when you converted the property. The IRS often scrutinizes these conversions, especially when there's a loss involved. Get a formal appraisal or at least a comparative market analysis from a realtor that you can keep with your tax records.
Wait, I thought Section 1231 losses always get ordinary loss treatment regardless of holding period? Isn't the 1 year+ holding period just for determining if gains get capital gains treatment? I've been doing my taxes wrong if that's not the case!
You're right that Section 1231 losses are treated as ordinary losses regardless of holding period. I should have been more precise in my explanation. What I was referring to is that to qualify as Section 1231 property in the first place, the property must be used in a trade or business and held for more than 1 year. Since the OP has held it for 2 years as a rental, it qualifies as Section 1231 property. If it had been held for 1 year or less as a rental, it wouldn't qualify for Section 1231 treatment, and would instead be subject to ordinary income/loss rules for property not used in a trade or business.
Has anyone here used the cost segregation strategy for rental properties? When I sold my rental last year at a loss, I wish I had done this earlier. Instead of depreciating the entire property over 27.5 years, you can break out components like appliances, carpet, etc. that have shorter depreciation periods (5, 7, or 15 years). This could potentially have increased your accumulated depreciation, lowered your adjusted basis further, and given you a larger Section 1231 loss to claim against your W2 income. Might be worth looking into before you sell.
I actually haven't heard of cost segregation before. That sounds really useful! Is it something I could still do now even though I've already been depreciating the property as a whole for 2 years? Or is it too late to change how I've been handling the depreciation?
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Be REALLY careful with this. What you've done could potentially be interpreted as money laundering or unlicensed money transmission depending on the amounts involved. There are specific regulations around acting as a money transmitter, especially with crypto. I'm not saying you did anything wrong intentionally, but the IRS might flag this transaction regardless of how you report it. If the amount was significant (over $10k) there are additional reporting requirements.
This is unnecessarily alarmist. Helping a friend one time doesn't make you a money transmitter business under FinCEN regulations. The money transmitter laws are for people regularly engaged in the business of transmission. A one-off favor doesn't qualify.
You're right that a single transaction probably wouldn't trigger money transmitter registration requirements, but it can still create reporting complications. FinCEN has been increasingly scrutinizing crypto transactions. What concerns me more is that banks and exchanges are filing suspicious activity reports for exactly this type of activity - receiving crypto and immediately cashing it out for someone else. While one transaction might not be an issue, it's important for OP to understand there are regulatory considerations beyond just tax reporting.
Has anyone considered that Coinbase might issue a 1099-K for this transaction? I had a similar situation last year (helped my cousin in Mexico sell some ETH) and Coinbase reported it on a 1099-K even though it wasn't my money. This created a huge headache because the IRS initially thought I had unreported income.
I think they only issue 1099-Ks if you exceed $20,000 in transactions AND more than 200 transactions in a year. Did you do a lot of other crypto trading? For 2023 taxes they were supposed to lower the threshold but they delayed that.
That used to be the case, but they've been inconsistent in my experience. I had less than $15k in total transactions for the year and definitely fewer than 200 transactions. They still issued one to me, which is why I warned about it. The reporting thresholds are supposed to change soon anyway, so better to be prepared.
Giovanni Marino
Just a heads up - I work in tax preparation and we see this type of discrepancy between digital and paper 1099s fairly often. Sometimes companies update the information after they've made the digital version available but before they print and mail the paper copies. If you're certain that both forms are for the same tax year and from the same company, the paper copy is almost always the final, correct version that gets reported to the IRS. The $100 difference might seem small, but it's better to file an amended return than risk getting a CP2000 notice later. Also, keep in mind that for 2022 returns, amendments are still paper forms that need to be mailed in - you can't e-file a 1040-X for that tax year. Make sure to include a brief explanation letter and copies of both 1099 forms to support your case.
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Fatima Al-Sayed
•Do they really care about such a small amount though? The tax difference would only be like $20-30. Seems like more trouble than it's worth to amend.
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Giovanni Marino
•While the IRS is certainly more concerned with larger discrepancies, their automated matching system flags all mismatches between reported income and what they received on information returns, regardless of the amount. A $100 discrepancy alone probably wouldn't trigger an audit, but it could trigger an automated CP2000 notice proposing additional tax, interest, and potentially penalties. When you receive such a notice, you'll end up having to respond anyway, and at that point, interest will have accrued. It's generally better to correct small issues proactively rather than dealing with IRS notices later. Plus, establishing a pattern of compliance and good faith corrections helps if you ever face more serious tax issues in the future. Think of it as an insurance policy against future headaches.
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Dylan Hughes
What happens if you ignore this? I've had small discrepancies on 1099s before and never amended anything. The IRS never contacted me about it.
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NightOwl42
•I ignored a similar situation with a $200 discrepancy back in 2020 and got a CP2000 notice about 18 months later. Had to pay the tax, plus interest, plus a 20% accuracy-related penalty. The penalty was small, but it was annoying to deal with. Definitely would just amend if I could do it over.
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