Anyone know if FreeTaxUSA lets you import your previous year's return if it was done with TurboTax? That's my biggest concern about switching.

I made the switch from TurboTax to FreeTaxUSA two years ago and it was one of the best financial decisions I've made. For your situation with W-2 income, mortgage interest, and charitable donations, FreeTaxUSA is absolutely perfect and will handle everything you need. The interface might look a bit dated compared to TurboTax's flashy design, but it's actually more straightforward - no upselling at every step trying to get you to upgrade to premium versions. The tax interview process asks all the right questions and the forms are clearly laid out. What really sealed the deal for me was the price difference - I was paying over $120 with TurboTax for federal and state, now I pay $15 total with FreeTaxUSA. The accuracy has been spot-on both years I've used it, and they have the same guarantees as the big names. My advice: give it a try this year. You can always start your return, see how it feels, and bail out if you're not comfortable (though I doubt you will be). The money you save will more than make up for any minor learning curve.

Just a heads up that if you set up your account for dividend reinvestment (DRIP), it slightly complicates your eventual capital gains calculations when you do sell in the future. Each reinvested dividend essentially creates a new lot of shares with its own cost basis and purchase date.

Great question! I went through the exact same confusion last year when I first started investing. Yes, you definitely need to report those dividends on your tax return even though you haven't sold anything. Here's the key thing to understand: dividends are taxable income the moment they're paid to you, regardless of whether you reinvest them or take them as cash. The IRS treats it as if you received the money and then chose to buy more shares with it. Make sure to bring your entire 1099 composite form to your tax prep appointment this weekend. Your preparer will need the dividend information from the 1099-DIV section. The empty 1099-B section is normal since you haven't sold anything yet. One tip: look at your 1099-DIV to see if any of your dividends are marked as "qualified dividends" - these get taxed at the lower capital gains rate instead of your regular income tax rate, which can save you money depending on your tax bracket. You're being smart by parking money for retirement and letting it grow long-term. Just remember that as long as you're receiving dividends, you'll need to report them each year even if you never sell the underlying investments.

Has anyone used TurboTax Self-Employed for this situation? I'm also a teacher with some side consulting work, and wondering if it's worth paying for that version vs just the regular one.

As someone who went through this exact transition from teacher-only income to teacher + 1099 freelance work, I can't stress enough how important it is to get organized NOW rather than waiting until tax season. The quarterly payment approach is definitely the safest route, but increasing your W-4 withholding at school is much more convenient if you can swing it. I'd recommend calculating about 25-30% of your expected freelance income and having that withheld from your teaching paychecks over the remaining pay periods. Don't forget to open a separate business checking account for your freelance income and expenses - it makes tracking everything SO much easier. And start keeping a simple spreadsheet or use an app to track every business expense from day one. Even small things like office supplies, software subscriptions, and mileage add up quickly. One thing I wish someone had told me: if you're making $38-50K in freelance income, you're definitely going to owe self-employment tax (15.3%) on top of regular income tax. Make sure whatever method you choose accounts for both!

Just a heads up that if you're looking for the 4-up vertical format, make sure you also get the right envelopes for them! The standard 4-up W2 forms need specific double-window envelopes (the W-2 Double Window Envelope 5-5/8" x 9"). Learned this the hard way last year and had to reorder everything.

For what it's worth, I've been dealing with this exact same issue for our small business. After trying several of the solutions mentioned here, I ended up going with a combination approach - I used the taxr.ai service that Jake mentioned to generate the proper 4-up template, then cross-referenced it with the IRS specifications I got through Claimyr to make sure everything was compliant. One thing I'd add is that if you're planning to do this annually, it might be worth investing in proper payroll software for next year. The one-time solutions work great when you're in a pinch, but having integrated W2 generation saves so much time and reduces errors. QuickBooks Desktop Pro includes the 4-up printing capability and often goes on sale around tax season. Also, definitely heed Lorenzo's advice about the envelopes if you're mailing - I made that same mistake and had to hand-fold everything into regular envelopes which was a nightmare!

I went through something very similar with a class action settlement from a defective smartphone case that damaged my phone back in 2022. Got $1,200 in late 2024 as reimbursement for the repair costs I paid out of pocket. The confusion around tax implications is totally understandable! In my case, I did receive a 1099-MISC in late January showing the full settlement amount. Following the advice of my tax preparer, I reported it on Schedule 1 as "Other Income" but then subtracted the same amount as a negative adjustment with the description "Class action settlement - recovery of repair costs." The key thing that helped me was keeping meticulous records of my original repair receipts and the settlement agreement language that specifically stated it was reimbursement for damages. Even though the 1099 made it look like taxable income, the documentation clearly showed it was just recovering money I had already spent. Don't stress too much about the W9 - like others mentioned, they collect everyone's info but the form itself doesn't determine taxability. The nature of what the settlement represents (reimbursement vs. punitive damages) is what matters for tax purposes. Since yours is clearly covering repair expenses you already paid, you should be in good shape!

I've been following this thread as someone who recently received a class action settlement as well, and wanted to add a few practical tips based on my experience with a medical device settlement last year. First, regarding the W9 timing - in my case, there was about a 6-week gap between submitting the W9 and receiving the 1099-MISC. The settlement administrator told me they batch process these forms, so don't worry if it seems like a long wait after submitting your paperwork. Second, when you do receive a 1099 (if you get one), take a photo or make a copy immediately. I learned this the hard way when my original got damaged and I had to request a duplicate, which delayed my tax filing by several weeks. Finally, for anyone using tax software to file, I found that TurboTax and H&R Block both have specific sections for handling settlement income that isn't actually taxable. Look for "Other Income" sections where you can add explanations - they've gotten better at guiding users through these situations since class action settlements have become more common. The consensus in this thread about keeping detailed records and not panicking about the 1099 is spot on. The settlement reimbursement itself isn't the issue - it's just making sure you report it correctly if you get the tax form!