Has anyone tried using the Free File Fillable Forms' built-in calculator for the depreciation tables? I'm finding the interface really clunky compared to the spreadsheets my accountant used to provide.

I've been doing my own taxes for about 3 years now after switching from an accountant, and I completely understand your situation! Here are a few practical tips that helped me: For Form 4562, you're right that it's not technically required if you have no new assets, but I'd recommend including it anyway to maintain consistency with your previous filings. It shows the IRS you're continuing to track your depreciation properly and can prevent questions later. One thing that really helped me was creating a simple spreadsheet to track all my existing assets and their remaining depreciation. I pulled this info from my last accountant-prepared return and then just update it each year. This makes filling out Form 4562 much easier. For statements in Free Fillable Forms, I create them as simple text documents that clearly state: "Statement for Form [X], Line [Y]" at the top, followed by my explanation. Keep them concise but detailed enough to justify your position. The IRS just wants to understand your reasoning. You're definitely not overthinking it - being careful on your first DIY return is smart! The transition from accountant to self-filing can be nerve-wracking, but you'll get the hang of it. Take your time and don't hesitate to call the IRS if you have specific questions about your unique situation.

One more thing to consider - if any of your non-covered securities were acquired through inheritance or gifts, the cost basis rules are different. For inherited securities, you generally get a stepped-up basis to the fair market value on the date of death. For gifted securities, it's more complicated and depends on whether the value went up or down since the original owner purchased them. If this applies to you, make sure you're using the correct basis method when entering these in FreeTaxUSA. The basis Morgan Stanley provides might not account for these special situations.

This is such a helpful thread! I'm dealing with a similar situation with Charles Schwab non-covered securities. One thing I'll add is that if you have wash sale adjustments on your non-covered securities, make sure those are properly reflected when you enter each transaction. My broker statement showed several wash sale loss disallowances that I initially missed when manually entering transactions. The IRS won't see these adjustments since the basis isn't reported to them, but you still need to account for them properly to avoid claiming losses you're not entitled to. FreeTaxUSA has specific fields for wash sale adjustments when you're entering individual transactions, so don't forget to check for those on your 1099-B!

Does anyone know if Sprintax specifically has a bulk import option for Fidelity? I'm in the same boat but with about 15 transactions, and I really don't want to enter them all manually if I don't have to.

For your specific situation with just 2 stock sales and a $0.26 loss, I'd recommend entering them separately to be completely compliant. Since it's only 2 transactions, the extra work is minimal compared to the peace of mind. However, I want to address something important that others touched on - Sprintax is generally designed for non-resident tax filing and may not be the best choice if you're a U.S. resident with investment income. Most major tax software like TurboTax, FreeTaxUSA, or H&R Block have much better investment reporting features including direct imports from Fidelity. If you're stuck with Sprintax for other reasons, you'll likely need to enter each transaction manually with the sale date, purchase date, proceeds, and cost basis for each stock. Make sure the total matches exactly what's on your 1099-B to avoid any automated matching issues with the IRS. The $0.26 loss will carry forward to future years if you can't use it this year, so it's worth reporting correctly even though the amount is small.

Just a heads up that if you refinanced last year, you might have TWO 1098 forms - one from each lender. Don't forget to add both when calculating your total mortgage interest! I almost missed this and would have underreported by $3,200.

Another thing to watch out for - if you paid any points when you got your mortgage, those should show up in Box 6 of your 1098. Points paid on a purchase mortgage are generally fully deductible in the year you bought the house, which could add a nice chunk to your itemized deductions. Since you bought in August, you might have paid origination points that you can deduct this year. Just make sure you didn't already deduct them if they were rolled into your mortgage amount rather than paid separately at closing.

Has anyone here actually calculated how many trades you need to qualify for trader tax status? I've heard different numbers from different accountants.

Just to add some clarity on the IRA question - your beneficiary IRA distributions will be taxed as ordinary income regardless of your trader status election. This is because IRAs don't have capital gains treatment to begin with. When you take distributions from a traditional IRA (including inherited ones), it's all ordinary income tax regardless of what investments were inside or how long they were held. So making the trader tax status election for your trading account won't make your IRA distributions any worse tax-wise - they were already going to be ordinary income. The election only affects your non-retirement trading account where you'd be giving up potential long-term capital gains treatment in exchange for the trader benefits like avoiding wash sales. Make sure you can handle losing long-term capital gains rates on any positions you might hold longer in your trading account before making this election.