Honestly, if you've been doing your own taxes since 2012, adding a 1099-SA and 1099-K isn't that big a jump in complexity. I'd try the DIY route first with a slightly better tax software than the free version. HR Block in person is crazy expensive for what you're describing - my sister paid $230 last year for something similar!

For your situation, I'd recommend starting with mid-tier tax software before jumping to in-person prep. TurboTax Deluxe or H&R Block Premium online will easily handle your 1099-SA and potential 1099-K for around $50-80, which is way less than the $150+ you'd pay in person. The 1099-SA is pretty straightforward - if you used your HSA money for qualified medical expenses, it's not taxable income. The 1099-K can look scary but it's just reporting payment processor transactions, not necessarily taxable income. You only owe taxes on actual profit from sales. Since you've been successfully filing your own taxes for over a decade, these additions aren't dramatically more complex. The software will walk you through both forms with interview-style questions. Save the money and try the DIY approach first - you can always go to a professional next year if you find it too complicated.

I'm in a very similar situation - small partnership that's been mostly dormant while waiting for our ERC to process. Based on all the responses here, I think I'm going to try TaxSlayer Business for around $70 since it seems like the most affordable option that still provides some guidance. The DIY route is tempting to save money, but I'm honestly worried about making mistakes on a partnership return, even a simple one. And while the taxr.ai recommendations are interesting, I'd rather stick with something more established for my first time doing this myself. Thanks everyone for the detailed breakdown of options - this thread has been incredibly helpful! It's reassuring to know there are affordable alternatives to the $200+ software packages.

I've been following this thread closely since I'm in an almost identical situation - partnership on hold waiting for ERC funds to come through. After reading all the suggestions here, I decided to go with TaxAct Business for around $80 this year. What really sold me was that several people mentioned it handles ERC-related entries well, which has been a concern of mine since our business situation is a bit unusual right now. The interface seemed more intuitive than TaxSlayer when I tried their demo, and the extra $10-15 felt worth it for the peace of mind. For anyone else in a similar boat, I'd recommend trying the free demos that most of these platforms offer before committing. It really helped me get a feel for which one would work best for my comfort level with tax software.

One thing I haven't seen mentioned yet is the importance of getting the appraisal documentation right. Since your lender is requiring the sale price to be listed at $650,000, make sure you get an independent appraisal that actually supports that value. The IRS could potentially challenge the gift of equity amount if the stated fair market value seems inflated. If the property truly appraises for $650,000, you're golden. But if it only appraises for, say, $500,000, then the actual gift would be $110,000 ($500k - $390k), not $260,000. This affects both the gift tax reporting for your in-laws and ensures the IRS doesn't question the transaction later. I'd recommend getting the appraisal done early in the process so you can adjust the numbers if needed before closing.

As someone who's worked in real estate tax planning, I'd strongly recommend getting both appraisals - one for the lender and an independent one for tax documentation. Many lenders will accept a slightly lower appraisal as long as the loan-to-value ratio still works with their requirements. The key is having solid documentation for the IRS that the fair market value supports your gift of equity calculation. If there's a significant discrepancy between appraisals, you'll want to understand why before closing. Sometimes it's just different methodologies, but occasionally it reveals that the initial value estimate was off. Also consider timing - if you can close this transaction in late December vs early January, it might give your in-laws more flexibility in managing the tax impact across different tax years. They could potentially make estimated payments or adjust withholdings to cover the additional tax liability.

I went through this exact same frustration last year! TurboTax definitely changed their policy on HSAs - it used to be included in the free version. The $120 total cost is outrageous for such a simple return. I ended up switching to FreeTaxUSA and it's been great. HSAs are handled completely free on the federal return, and state filing is only $15. The interface isn't as flashy as TurboTax but it walks you through everything clearly. I've used it for two years now with my HSA and haven't had any issues. The IRS Free File program is also worth checking if your AGI is under $73K - several participating companies offer completely free filing including HSA support. Don't let TurboTax's marketing fool you into thinking you need their overpriced service for something this basic!

I've been using TaxAct for the past few years and they still include HSAs in their free federal filing. Like others mentioned, the tax software companies have definitely been pushing more "basic" forms into paid tiers - it's really frustrating. One thing to watch out for with any free service: make sure you're actually using the truly free version and not getting upsold during the process. I almost got tricked into paying for "audit protection" and other add-ons that I didn't need. Also, since your situation is simple (single, standard deduction, just the HSA), you might want to consider doing it by hand with the IRS Free File Fillable Forms. Form 8889 for HSAs really isn't that complicated if you're just reporting employer contributions and not taking distributions. There are good instructions on the IRS website, and you'd save money while learning more about your taxes.

Great question, Ravi! I went through something very similar with a research stipend a couple years ago. Here are the key things I learned: 1. **You'll get a 1099-NEC** - The organization will send you (and the IRS) a 1099-NEC form showing the $4,000 as non-employee compensation. 2. **Self-employment tax applies** - You'll owe the full 15.3% self-employment tax (normally split between employer/employee), plus regular income tax on top of that. 3. **Quarterly payments** - With $4,000, you'll likely owe around $600-800 in self-employment tax alone, plus income tax depending on your bracket. Since this could easily put you over the $1,000 threshold, I'd recommend making quarterly estimated payments to avoid penalties. 4. **Track expenses** - Keep receipts for anything directly related to your internship - supplies, travel, home office space if you work remotely, etc. These can reduce your taxable income. 5. **File Schedule C** - You'll report this income and any deductions on Schedule C (Profit or Loss from Business) with your regular tax return. My advice: Set aside 30% of each stipend payment immediately. Better to have too much saved than scramble to pay a big tax bill later! The IRS doesn't mess around with self-employment tax. Good luck with the internship!

This is really helpful information everyone! As someone who just went through this exact situation with a summer research stipend, I wanted to add a few practical tips: **Timing matters for quarterly payments** - Since your internship runs April-June, you'll want to make your first estimated payment by June 15th (for the April-June quarter). Don't wait until September 15th or you might face penalties. **Keep a simple spreadsheet** - Track every payment you receive and immediately transfer 30% to a separate "tax savings" account. I learned this the hard way when I spent my tax money and had to scramble in April! **Consider state taxes too** - Don't forget that most states will also want their cut of your stipend income. The rules vary by state, but you'll likely need to make quarterly payments there too. **Get organized early** - Start a folder (physical or digital) for all internship-related receipts and documents. Even small expenses like notebooks or software subscriptions can add up to meaningful deductions. One last thing - if you're a student, make sure this income doesn't affect your financial aid eligibility. Some aid packages have earnings limits that could be impacted by self-employment income. Hope this helps, and congratulations on the internship!