I completely understand your frustration! I went through the exact same thing with our small condo association last year. The good news is that your situation is actually much simpler than you think - you're just using the wrong form. Based on what you've described (member contributions for shared expenses like water/sewer), your condo trust almost certainly qualifies to file Form 1120-H instead of Form 1041. This form was specifically designed for homeowners associations and small condo associations like yours. Here's why 1120-H would be perfect for you: - Your $9,000 in member contributions would be "exempt function income" (completely tax-free) - The $8,200 water/sewer expenses are fully deductible - The $85 bank fees are also fully deductible - You'd only pay taxes on investment income (which you don't have) at a flat 30% rate To qualify, you need 60% of income from member dues (you're at 100%) and 90% of expenses for property maintenance (water/sewer clearly qualifies). You make the election simply by filing 1120-H instead of 1041 - no separate paperwork needed. This would eliminate all your confusion about where numbers go on the 1041 because the 1120-H is designed specifically for situations like yours. I wish someone had told me this before I spent hours wrestling with trust accounting principles that don't really apply to condo associations!

I've been helping small condo associations with their tax filings for years, and you're absolutely right to feel frustrated - Form 1041 really wasn't designed for simple condo maintenance situations like yours. The consensus in this thread about Form 1120-H is spot on. Your situation is actually a textbook case for Section 528 treatment: 100% of income from member assessments, expenses clearly for property maintenance, and a straightforward two-unit structure. One additional tip that might help: when you do switch to Form 1120-H, keep detailed records of your qualifying expenses. The IRS occasionally audits small associations, and having clear documentation that your expenses are for "exempt function" purposes (like your water/sewer bills) makes everything smooth sailing. Also, don't feel bad about the confusion with TaxAct - most commercial tax software is terrible for HOAs and condo associations because we're such a niche market. The software assumes you're a traditional trust with beneficiaries, complex distributions, etc., when really you're just neighbors sharing utility bills. Make the switch to 1120-H and you'll wonder why anyone ever told small condo associations to file 1041s in the first place!

This is such valuable information! I've been doing my own taxes with TurboTax for years but always stress about whether I'm missing deductions or making mistakes. The fact that VITA has trained volunteers AND a quality review process actually sounds more thorough than what I get doing it myself. One question - do they handle situations where you have multiple W-2s from different jobs during the year? I switched jobs in 2024 and have two W-2s, plus I contributed to both a traditional and Roth IRA. Would that be considered too complex for VITA or is that pretty standard stuff they can handle? Also wondering about timing - when do these programs typically start taking appointments for the current tax season? I always like to file early to get my refund quickly.

I wish I had known about VITA years ago! I've been paying H&R Block around $300 every year for what's essentially a basic return - just my W-2, some student loan interest, and the standard deduction. Reading through everyone's experiences here, it sounds like VITA would have been perfect for my situation and saved me thousands over the years. The quality review process actually gives me more confidence than some of the chain tax prep places where you never know if you're getting someone experienced or a seasonal worker who just finished their training. The fact that these are volunteers who choose to help their community rather than employees trying to upsell services is really appealing. I'm definitely going to look into this for next year's taxes. For anyone else on the fence - it seems like the worst case scenario is you find out your situation is too complex and you're back where you started, but the potential savings and peace of mind from the quality review process make it worth trying. Thanks to everyone who shared their experiences!

Another quirk to be aware of - qualified dividends! If your synthetic long crosses an ex-dividend date, any dividend equivalents you effectively receive aren't eligible for qualified dividend tax treatment. With actual share ownership, you can get the preferential qualified dividend tax rate if you meet the holding period requirements. But with a synthetic long, you're technically not receiving dividends - you're just seeing the options prices adjust to account for the dividend. So any dividend benefit gets taxed as ordinary income through the options pricing.

This is a great discussion on a complex topic. One thing I'd add is that the IRS has been increasingly scrutinizing synthetic positions in recent years, especially when traders use them to manufacture tax losses while maintaining economic exposure to the underlying asset. The wash sale treatment that @Andre Lefebvre mentioned is definitely the correct approach for scenario 2. What many people don't realize is that the IRS views the entire synthetic long strategy as a single integrated transaction, not separate option trades. This is why timing the individual legs differently doesn't necessarily help you avoid wash sale treatment. I'd also recommend keeping very detailed records of your synthetic positions, including the dates opened, premiums paid/received, and your intent when entering the strategy. If you get audited, being able to demonstrate that this was part of a legitimate investment strategy (rather than tax loss harvesting) will be important. The key principle to remember is that tax treatment should follow economic substance. Since a synthetic long has the same risk/reward profile as owning shares outright, the IRS expects the tax consequences to be similar as well.

Just wanted to add one important point that might help you - make sure you keep all your relocation documentation organized! I learned this the hard way when I got audited two years after my relocation. The IRS wanted to see receipts for everything my company paid for, even though it was already reported on my W-2. Keep copies of your relocation agreement, receipts for moving expenses, temporary housing documentation, and any correspondence with your employer about the benefits. Even though you can't deduct most moving expenses anymore, having this paper trail saved me during my audit when I had to prove the amounts were legitimate business relocations and not just additional compensation. Also, if you're relocating across state lines, double-check if your new state has any special rules about taxing relocation benefits. Some states treat them differently than the federal government does.

One thing I haven't seen mentioned yet is timing - when you receive your relocation benefits can affect which tax year they're reported in. If your company paid some expenses in December 2024 but others in January 2025, they might be split across different W-2s. Also, be aware that some companies use third-party relocation management companies (like Cartus or SIRVA) to handle the payments. In those cases, you might receive a separate tax document from the relocation company in addition to your regular W-2 from your employer. Don't panic if you get multiple tax forms - just make sure you report all the income. And here's something that caught me off guard: if your company provided temporary living expenses that exceeded the federal per diem rates for your area, the excess amount is definitely taxable and should be clearly identified on your tax documents. Worth checking if you stayed in expensive temporary housing!

For anyone using QuickBooks, there's a specific way to handle this. Set up a separate account for sales tax collected, and when you run reports, make sure to exclude that account from your income reports. Then when you pay the tax to the state, it zeros out that account. Your 1099K will still show the full amount, but your accounting will clearly show what was sales tax vs actual income.

This is such a helpful thread! I'm dealing with a similar situation but with Amazon FBA sales. Amazon collected and remitted sales tax on my behalf in multiple states, but my 1099-K shows the gross amount including all that tax. One thing I learned from my CPA is to make sure you have documentation showing which portion of your 1099-K represents sales tax that was remitted by the marketplace vs. sales tax you collected and paid yourself. Amazon provides monthly settlement reports that break this down clearly. Also, if you're using estimated tax payments for next year, remember to base your calculations on your actual taxable income (after deducting the sales tax), not the inflated 1099-K amount. I almost overpaid my Q1 estimated payment because I was using the wrong baseline number!