Has anyone tried using the IRS's own free file options? I'm wondering if those let you itemize for free too. The commercial options all seem to have some kind of catch.

I went through this exact same situation last year! H&R Block kept pushing their $35 upgrade on me too. What I learned is that they're technically correct about the potential savings, but you definitely don't need to pay them for it. Here's what I'd recommend: First, gather up all your tax documents - mortgage interest statement (1098), medical bills, charitable donations, property tax records, etc. Then add them up yourself to see if they exceed the standard deduction ($13,850 if you're single, $27,700 if married filing jointly). If your itemized deductions are legitimately higher than the standard amount, then yes, you should itemize. But don't pay H&R Block for it! I switched to FreeTaxUSA mid-process last year and saved the upgrade fee while still getting the higher refund. Their interface is actually cleaner than H&R Block's too. The key thing to remember is that H&R Block's "free" version is really just a marketing tool to get you to upgrade. Other services like FreeTaxUSA, TaxAct, and the IRS Free File options include itemizing in their actual free versions.

I'm actually a landlord with multiple properties and just want to add one more thing that hasn't been mentioned yet: depreciation recapture! Even after you figure out your correct adjusted basis, when you sell a rental property, you'll have to "recapture" the depreciation you claimed over the years at a 25% tax rate (which is often higher than the long-term capital gains rate). So make sure you're planning for that tax hit too. It catches a lot of first-time rental property sellers by surprise.

Your accountant is being overly cautious here. The key distinction is between capital improvements (which get depreciated and added to basis) versus regular repairs/maintenance (which are fully deducted and don't affect basis). For your $23,000 in improvements - items like a new roof, water heater, and flooring are typically capital improvements that should have been depreciated over time, not fully deducted in one year. These DO increase your cost basis, but you need to reduce your basis by any depreciation you've already claimed. The confusion often comes from incorrect tax treatment in prior years. Many taxpayers (and some preparers) mistakenly deduct capital improvements as current expenses instead of depreciating them. If this happened, you might need to determine what should have been depreciated versus what was correctly expensed. I'd recommend getting a second opinion or asking your accountant to specifically explain which of your $23,000 in improvements they believe were correctly treated as immediate deductions versus which should have been capitalized. The IRS Publication 527 has detailed guidance on this distinction for rental properties. Don't let them dismiss legitimate basis increases - this could cost you thousands in unnecessary capital gains tax.

Just want to make sure the OP and others understand capital gains taxes for 2025 filing. If you hold your investments for more than a year before selling (long-term capital gains), you get a much better tax rate (0%, 15%, or 20% depending on your income) than short-term gains (taxed as ordinary income). Making this distinction could literally save you thousands on your tax bill! I learned this the hard way when I day-traded some stocks and got hit with ordinary income rates on everything.

Great advice from everyone here! Just want to add one more consideration for @Ava Kim - since you're working at Target and trading stocks, you might want to look into tax-loss harvesting if you have any losing positions. You can sell losing stocks to offset your capital gains, which reduces your overall tax liability. For example, if you made $30k in gains but also have $10k in unrealized losses, you could sell those losing positions to bring your taxable gains down to $20k. You can even carry forward losses beyond your gains (up to $3k per year against ordinary income). This strategy works best when combined with the estimated payment approaches others mentioned. Just make sure to avoid the wash sale rule - don't buy back the same or "substantially identical" securities within 30 days of selling for a loss, or the IRS will disallow the loss deduction.

I'm so glad I found this thread! I'm dealing with the exact same situation - had to close my small business (selling handmade soaps) earlier this year and kept about $450 worth of remaining inventory for personal use. Reading through everyone's experiences here has been incredibly reassuring. I was also getting those frustrating TurboTax errors when trying to enter negative purchase amounts, and I was starting to worry I was doing something fundamentally wrong. The consensus approach seems crystal clear now: - Line 35: Beginning inventory ($450 in my case) - Line 36: Purchases ($0) - Line 40: Other costs - "inventory withdrawn for personal use" ($450) - Line 41: Ending inventory ($0) The "selling to yourself at cost" analogy really helps me understand why this creates a neutral business impact. I'm not generating income or creating a deductible loss - I'm just closing out the business inventory by transferring it to personal use at exactly what I originally paid. One thing I'm curious about - has anyone had their return reviewed or audited when using this approach? I want to make sure this method is rock-solid from an IRS perspective, especially since it seems like such a common point of confusion for small business owners. Thanks to everyone who shared their real-world examples and numbers. Connor, Dylan, Carmen, and others - seeing your actual situations makes this so much less intimidating!

This thread has been absolutely invaluable! I was in the exact same boat as Marcus - closed my small photography props rental business after a tough year and had about $825 in remaining inventory (backdrops, lighting equipment, small props) that I decided to keep for personal photography projects. Like everyone else, I initially tried to enter this as a negative purchase in TurboTax and kept getting those frustrating validation errors. After reading through all these detailed explanations and real-world examples, I finally understand why that approach doesn't work. The method that worked perfectly for me: - Line 35: Beginning inventory ($825) - Line 36: Purchases ($0) - Line 40: Other costs - "inventory withdrawn for personal use" ($825) - Line 41: Ending inventory ($0) Result: Cost of Goods Sold = $0, which makes perfect sense since I had no sales. The mental framework that really clicked for me was thinking of it as "closing out" the business inventory rather than trying to create some kind of transaction. I'm not selling to myself, I'm not creating a business expense - I'm simply removing inventory from the business books because the business no longer exists. I also took everyone's advice about documentation seriously. Created a detailed spreadsheet listing every item I kept with its original purchase price, totaling exactly $825. This gives me peace of mind for the current filing and will be essential if I ever sell any of these items personally in the future. Thanks to Marcus for asking the original question and to everyone who shared their experiences - Carmen, Connor, Emma, Fatima, and all the others. This community approach to solving tax problems is amazing!

Great thread everyone! I just want to emphasize something that might not be obvious - the "multiple jobs" checkbox on the W-4 actually uses a pretty simplified calculation that assumes both jobs are worked simultaneously for the full year. Since you started your restaurant job recently, you might get more accurate withholding by skipping that checkbox entirely and instead calculating the exact additional withholding needed using line 4(c). Here's why: The multiple jobs checkbox essentially takes your annual income from the higher-paying job, finds the tax on that amount, then finds the tax on your total combined income, and withholds the difference. But if you only worked the second job for part of the year, this creates an over-withholding situation. For your situation ($42K main job + partial year restaurant work), I'd recommend: 1. Use the IRS withholding estimator with your actual start date for the restaurant job 2. Input realistic projections for your restaurant earnings through year-end 3. Use the specific dollar amount it recommends for line 4(c) rather than the checkbox This approach has worked really well for me with seasonal and mid-year job changes. You'll get much more precise withholding that accounts for the actual timing of your income rather than the simplified assumptions built into the multiple jobs checkbox.

This is such a helpful thread! I'm dealing with a similar situation - just started a part-time evening job at a retail store while keeping my full-time day job. Reading through all these responses, it sounds like the key takeaway is to be really careful about not under-withholding. One thing I'm curious about that I didn't see mentioned - how do bonuses from either job factor into this? My main job gives annual bonuses in December, and I'm wondering if that could throw off my withholding calculations since it's hard to predict the exact amount. Also, for those who have used the IRS Tax Withholding Estimator, how user-friendly is it really? I tried using some online tax calculators before and they were confusing as heck. Is the official IRS one actually easier to navigate? Thanks to everyone sharing their experiences - this is exactly the kind of real-world advice I needed to hear!