Just wanted to add another perspective on installment sales since Malik brought it up - they can be incredibly effective for business sales, but there are some important considerations to keep in mind. Most business assets can qualify for installment sale treatment, but there's a key exception: inventory and depreciation recapture on personal property (like your laundry equipment) generally cannot use installment treatment. This means the depreciation recapture portion would still hit you in year one, even with an installment sale structure. However, the portion of your sale allocated to goodwill, customer relationships, and other intangible assets CAN qualify for installment treatment. So you'd still get some benefit from spreading those gains over multiple years. The buyer would need to agree to seller financing for a true installment sale. Alternatively, if they want to pay cash upfront, you could potentially structure it as a sale to a buyer who then immediately sells to the actual purchaser with seller financing - though this gets complicated and you'd definitely need legal and tax counsel. Another option to consider is a charitable remainder trust if you're charitably inclined. You can transfer the business to the trust, get a partial tax deduction, receive income for life, and potentially reduce the overall tax bite significantly. Not right for everyone, but worth exploring given the size of your transaction.

This is such a great discussion! As someone who recently went through a similar business sale, I wanted to add one more consideration that hasn't been mentioned yet. Make sure you understand the difference between asset sales vs. stock sales, as this can significantly impact your tax treatment. Most small business sales (especially laundromats) are structured as asset sales, which is what everyone has been discussing here with the depreciation recapture. However, if your business is incorporated and you can structure it as a stock sale instead, you might get more favorable capital gains treatment on the entire transaction. The downside is that buyers often prefer asset sales because they can "step up" the basis of assets for their own depreciation purposes. Also, don't forget about state tax implications! Some states have no capital gains tax, while others tax capital gains as ordinary income. Depending on where you're located, this could be another significant factor in your planning. Given the complexity everyone has outlined here - depreciation recapture, asset allocation, installment sales, appraisals - I'd strongly recommend getting multiple opinions from tax professionals who specialize in business sales. The potential savings from proper planning on a $300k transaction could easily justify the cost of expert advice. Best of luck with your sale and retirement! 25 years running a business is quite an accomplishment.

I went through something very similar with Treasury bonds last year. One thing that helped me was understanding that the $675 accrued market discount on your 1099-B is essentially the taxable portion of your $1,000 total gain ($13,000 - $12,000). The difference between your total gain and the reported market discount likely accounts for the accrued interest and any other adjustments your broker made. When you enter this in your tax software, you'll report the $675 as ordinary income (not capital gains) and it gets added to your regular income. Combined with your $65 interest from the 1099-INT, you're looking at about $740 in additional taxable income from this bond. The key thing to remember is that even though your 1099-B shows no capital gain/loss, the IRS still wants their cut of the "built-in gain" you received by buying the bond at a discount. It's counterintuitive but that's how the tax code works for market discount bonds.

Just to add another perspective on this - I had a similar bond situation last year and made the mistake of trying to handle it myself initially. The tax software questions about market discount elections are confusing because they're asking about a choice most individual investors never make. Here's what I learned: When your 1099-B shows "Accrued Market Discount," that's money you need to report as ordinary income (taxed at your regular rates, not capital gains rates). The reason your Cost Basis equals Proceeds is because your broker already adjusted your basis to account for the market discount - but you still owe taxes on that discount amount. Think of it this way: You bought a $13,000 bond for $12,000. The IRS considers $675 of that $1,000 difference as taxable income that you earned by holding the bond. Even though you didn't receive a separate payment for it, it's built into the redemption value. So yes, you'll be taxed on $740 total ($675 market discount + $65 interest). Make sure when your tax software asks about including the market discount in current year income, you select "yes" - that's the normal treatment for most people who haven't made special elections about annual amortization.

Something to consider - you might also want to look at tax-loss harvesting before year-end to potentially lower your MAGI. If you have any investments with unrealized losses, selling them could offset some of your gains and potentially get you under the threshold.

Just to add another perspective - if you're really close to the income limits, you might also want to consider maximizing your 401(k) contributions if you haven't already. Traditional 401(k) contributions reduce your AGI (and therefore your MAGI), which could potentially bring you back under the Roth IRA phase-out range. For 2025, you can contribute up to $23,500 to a 401(k) ($31,000 if you're 50 or older). Even if you can't max it out completely, every dollar you contribute reduces your MAGI dollar-for-dollar. This strategy works especially well if your employer offers matching contributions too.

FYI - If you drive primarily for 1099 work, you might want to keep a dedicated credit card JUST for vehicle expenses. That's what I do for my DoorDash work - everything car-related goes on one card, which makes it super easy to calculate percentages for business use vs personal use at tax time.

Just want to add another perspective here - I'm a tax preparer and see this situation constantly with gig workers. The good news is you're not completely out of luck, but you do need to be strategic about how you approach this. First, DON'T just estimate or guess at your mileage without any supporting documentation. That's asking for trouble if you get audited. The IRS expects "adequate records" which means some form of contemporaneous tracking OR a reasonable reconstruction method with supporting evidence. Your delivery apps are your best friend here. Most platforms (DoorDash, UberEats, etc.) keep detailed trip histories that include pickup/dropoff locations and timestamps. Download all of this data ASAP - some platforms only keep it for a limited time. You can use mapping tools to calculate the actual mileage between locations and build a defensible log. For your $4,300 in gas receipts - these could still be valuable if you choose the actual expense method, but you'll need to determine your business use percentage. Without proper records, this becomes much harder to defend. Consider consulting with a tax professional before filing. The potential deduction savings (likely several thousand dollars) usually justify the cost of getting expert guidance on your specific situation.

I'm curious about the timeline here...when did you file your original return and how long do you typically have to amend? My tax guy always says "don't worry about small stuff" but reading these comments has me wondering if that's good advice.

I went through this exact same situation a couple years ago with a part-time retail job I'd forgotten about. The amount was similar to yours - around $1,100. I was tempted to just ignore it since it seemed so small, but I'm really glad I didn't. Here's what I learned: the IRS matching system is pretty sophisticated. They get copies of all W-2s and 1099s, and their computers automatically flag when reported income doesn't match what employers submitted. You'll likely get a CP2000 notice in 12-18 months asking about the discrepancy, and by then you'll owe penalties and interest on top of the additional tax. Filing the 1040-X now while it's still voluntary shows good faith and typically results in minimal or no penalties. Plus, if they withheld any federal taxes from your paychecks (which many part-time jobs do), you might actually end up with a small additional refund rather than owing money. The amended return process isn't as scary as it sounds - just recalculate your tax with the additional income included and submit the form. Much better to handle it proactively than wait for the IRS to find it themselves!