I went through this exact situation last year and learned a few hard lessons that might help you avoid my mistakes. First, when you amend your return, make sure you also calculate and pay any penalties for late payment since the IRS considers fellowship income as earned throughout the year, not just when you file. For entering it in TurboTax, go to Federal > Income & Expenses > Less Common Income > Other Reportable Income. Look for "Other Income Types" and select "Other Income Not Already Reported." Enter your fellowship stipend amount and put "Fellowship" in the description field. One thing nobody mentioned yet - if your fellowship is over $600 and you didn't receive a 1099, you technically should file Form 1099-MISC for yourself (weird, I know). Not everyone does this, but it's technically required. Also, don't forget that you'll owe self-employment tax on the fellowship income since it's not subject to payroll taxes. The quarterly estimated payments you're planning are smart, but calculate them based on your total expected tax liability, not just the fellowship portion. Use Form 1040-ES and remember the safe harbor rule - if you pay 100% of last year's tax liability through quarterlies, you won't owe penalties even if you end up owing more.

I went through this exact same situation during my first year of grad school! You're definitely not alone in being confused - fellowship income is one of those weird tax situations that most software and support staff don't handle well. For TurboTax specifically, here's what worked for me: Go to Federal > Income & Expenses > Less Common Income, then look for "Other Income" or "Miscellaneous Income." There should be an option for scholarship/fellowship income that wasn't reported on a tax form. Enter just the stipend portion (living expenses) as taxable income - not the tuition or fees that went directly to the school. One tip that saved me a lot of headache: contact your graduate school's financial aid office and ask for a "fellowship tax allocation letter." They can break down exactly what portion went to qualified education expenses (tuition, fees, required books) versus your taxable stipend. Most schools can provide this even if they don't automatically issue tax forms. Also, you're absolutely right to plan quarterly payments for 2024! Fellowship recipients are technically considered self-employed for estimated tax purposes, so you'll want to use Form 1040-ES to calculate those payments. It's much easier than dealing with amendments later. The good news is that fellowship stipends are only subject to regular income tax, not self-employment tax, so at least you don't have to worry about that additional 15.3%!

For organizing your K-1 records over multiple years, I'd recommend creating a master folder for the entire investment, then subfolders by tax year. Each year's folder should include your K-1, any supplemental statements, correspondence with the syndication, and copies of the relevant pages from your tax return where you reported the K-1 items. Also keep a running spreadsheet tracking your basis in the investment - this starts with your initial investment amount and gets adjusted each year by your share of income, losses, and distributions. You'll need this basis information when the property eventually sells to calculate your gain/loss correctly. For apartment building investments like yours, you should definitely qualify for the QBI deduction under the rental activity rules. Just make sure the syndication provides you with the qualified business income amount and the allocable W-2 wages in their Section 199A information (Code Z). One more thing - if your syndication issues any corrected K-1s later (which unfortunately happens sometimes), don't panic. Just amend your return again with the corrected information. The IRS understands that partnership tax reporting can be complex and corrections are common.

Regarding corrected K-1s, they typically come out within 30-60 days after the original K-1s if there are going to be corrections. Most well-organized syndications get it right the first time, but corrections can happen due to late-arriving information from property managers, final audit adjustments, or errors in calculations. Given that you're already running late on your amendment, I'd suggest reaching out to your syndication one more time (via email if phone isn't working) to ask specifically if they expect any corrections to the K-1s they've already issued. If they say no or don't respond within a few days, go ahead and file your amendment with what you have. The IRS understands that partnership investors are often at the mercy of when they receive their K-1s, and filing an amended return due to a corrected K-1 is a legitimate reason that won't cause any penalties. It's better to get your amendment filed than to keep waiting indefinitely. Also, since this is your first real estate syndication, you might want to consider working with a tax professional who has experience with partnership returns, at least for this first year. The complexity can be overwhelming, and having someone guide you through it can save you time and ensure you're not missing any deductions or making costly mistakes. Many CPAs offer consultation services specifically for K-1 issues during tax season.

Hey, just wanted to chime in with real numbers from my experience switching from W-2 ($75k) to 1099 ($103k) last year. After all the math, I'm taking home about $4,200 more per year as a 1099, but I'm working way more hours and don't have paid vacation anymore. For me, the biggest advantages were: 1. I can contribute over $30k to my Solo 401k vs the $20.5k limit I had as an employee 2. Being able to deduct my home office, new computer, software, and even part of my cell phone bill 3. Having more control over my schedule The biggest downsides: 1. Paying quarterly estimated taxes (easy to mess up) 2. No employer health insurance (I'm paying $487/month now on the marketplace) 3. Unpaid vacation and sick days 4. Constantly worrying about documentation for deductions

One thing to consider that hasn't been fully addressed is the stability factor. As a W-2 employee, you have some job protection and unemployment benefits if things go south. As a 1099 contractor, you can be let go at any time with zero notice and no unemployment safety net. I'd also recommend getting a solid contract in place that clearly defines the scope of work, payment terms, and termination clauses. Make sure you understand whether this is truly a contractor role or if you're just being misclassified to save the company money on benefits and payroll taxes. The $24k difference ($92k vs $68k) sounds attractive, but remember you'll lose employer-paid benefits like health insurance, 401k matching, paid time off, and potentially other perks. When I made a similar switch, I calculated that my employer benefits were worth about $18k annually, so factor that into your comparison. If you do decide to go the 1099 route, definitely set aside 25-30% of each payment for taxes immediately. Open a separate business checking account and treat it like it's not your money - because it's not, it belongs to the IRS!

Just wanted to add that I tried a similar strategy a few years ago with a BVI corporation for my trading activity. Ended up paying over $45,000 in penalties and back taxes when I got flagged for audit. The IRS agent told me they specifically look for US traders trying to route activities through Caribbean tax havens.

I've been researching similar offshore strategies for my trading business and I have to echo what others have said - the risks far outweigh any potential benefits. The IRS has really cracked down on these structures over the past decade. What changed my perspective was learning about the "economic substance doctrine" - even if you technically follow all the rules for setting up an offshore entity, the IRS can still challenge it if there's no legitimate business purpose beyond tax avoidance. For day trading, it's really hard to establish genuine economic substance in the Cayman Islands when you're sitting at your computer in the US making all the trades. I ended up working with a tax professional who specialized in trader tax status and found legitimate domestic strategies that actually reduced my tax burden more than I expected. Things like proper entity selection, maximizing business expense deductions, and qualifying for trader tax status can make a significant difference without the compliance nightmare and legal risks of offshore structures. The reporting requirements alone for foreign entities would probably cost you more in professional fees than you'd save in taxes, not to mention the constant worry about whether you're crossing the line into evasion territory.

Check your AGI too! I had this exact problem and discovered TurboTax was incorrectly applying a phase-out to my mortgage interest deduction because my income was over a certain threshold. The software was calculating it wrong though. If your Adjusted Gross Income is over $250,000 (married) or $125,000 (single), TurboTax sometimes incorrectly applies limitations. That might explain why it's disappearing when you add the second mortgage - the combined amount might be triggering some faulty logic in their calculations.

I'm a tax professional and I see this TurboTax issue frequently with clients who own multiple properties in the same year. The software often has trouble handling the transition from one primary residence to another, especially when there's overlap with mortgage interest reporting. Here's what I recommend: Go to the "Forms" view in TurboTax and look at your Schedule A directly. Check if both mortgage interest amounts are showing up there. If they are, but your total deduction is wrong, there might be an issue with how TurboTax is calculating the limitation based on your loan amounts or dates. Also, make sure you're not accidentally double-entering information. Sometimes people enter mortgage interest in both the "Home Mortgage Interest" section AND the "Investment Interest" section, which can cause the software to remove deductions to avoid double-counting. If all else fails, you can manually override the mortgage interest deduction on Schedule A. Just make sure you have proper documentation (your 1098 forms) to support the amounts you're claiming.