Has anyone just tried using an online tax portal that automatically imports your 1099 data? I've been using TurboTax Self-Employed and it pulls a lot of my 1099 info directly from the IRS database before I even receive the physical forms from clients.

I'm dealing with a similar situation with one of my clients. What I've found helpful is being proactive about it - I send them a gentle reminder email in mid-December that includes my current W9 form (even though they should already have it) and a note about the January 31st deadline. I phrase it as "helping them stay compliant" rather than demanding something from them. I also keep detailed records of all payments throughout the year using a simple spreadsheet, so I can file my taxes with or without their 1099. But you're absolutely right that they have a legal obligation to send it without you having to ask. The fact that you have to chase them down every year suggests their accounting processes need improvement. If the gentle reminder approach doesn't work this year, you might consider mentioning the potential penalties they face for late filing - sometimes small organizations just aren't aware of the consequences.

If your bonus pushed you from the 22% to the 24% bracket, for example, remember that our tax system is progressive. Only the dollars that fall into that higher bracket get taxed at the higher rate. The rest of your income is still taxed at the lower rates of the brackets below it. But a large bonus can definitely cause underwithholding if your employer only withheld at the standard 22% supplemental wage rate. For 2025, single filers hit the 24% bracket at $95,376, the 32% bracket at $182,101, and the 35% bracket at $231,251. Married filing jointly has different thresholds.

I went through this exact same situation last year! Got a large bonus that was about 30% of my salary and ended up owing $2,100 even though my employer withheld taxes. What helped me understand it was realizing that the 22% flat withholding rate on bonuses is often not enough when you factor in state taxes, FICA taxes on the bonus amount, and how it affects your overall tax bracket. One thing that caught me off guard was that my bonus also pushed me over the income limit for some tax credits I'd been getting in previous years. The loss of those credits added to what I owed on top of the underwithholding issue. For this year, I updated my W-4 to have extra withholding throughout the year to cover any bonus I might receive. I'd rather get a smaller refund than owe a big chunk again. Also consider making a quarterly estimated payment if you know a bonus is coming - you can avoid underpayment penalties that way.

I went through something very similar when I purchased a small accounting practice last year. One thing I learned that might help you - make sure you're crystal clear about whether any part of your $27k included a non-compete agreement with the previous owner. Even if it wasn't explicitly called out in your contract, if there was any understanding that the seller wouldn't compete with you for a certain period, that portion needs to be amortized differently. Also, don't forget to consider if any of the customer contracts you acquired have specific terms or remaining durations. Sometimes part of the purchase price can be allocated to these existing contracts, which might have different tax treatment than pure goodwill. Your tax professional will definitely help sort this out, but having these details ready will make that meeting much more productive. Good luck with the expanded business!

Great discussion here! Just wanted to add one more important consideration for your meeting with the tax professional - make sure to discuss the potential impact on your state taxes as well. While federal tax law requires the 15-year amortization for goodwill, some states have different rules or additional requirements for business acquisitions. Also, since you mentioned this was a competitor buyout, keep detailed records of any costs associated with integrating their operations into yours (like transferring contracts, updating insurance, etc.). Some of these transition costs might be immediately deductible as business expenses rather than part of the asset purchase. One last tip - if your business grows significantly as a result of this acquisition, you might want to consider whether you need to change your business structure (LLC vs S-Corp, etc.). The additional income combined with the amortization deductions could affect your overall tax strategy. Your tax pro can run some projections to see if there are better approaches for your specific situation.

Has anyone used TurboTax to report their short-term rental income? I'm trying to figure out if the basic version will handle this or if I need to upgrade to the premium version.

One thing I haven't seen mentioned yet is the importance of keeping a detailed calendar or log of your rental activity. Since you're using the basement personally when family visits, you'll want to document exactly which days were: 1. Rented to paying guests 2. Available for rent but vacant 3. Used personally by you or family 4. Unavailable due to maintenance/repairs The IRS can be pretty strict about this documentation if you get audited. I use a simple spreadsheet with columns for date, status (rented/available/personal/maintenance), and any notes about bookings or personal use. Also, since you mentioned you sometimes let family stay there when they visit - make sure you're not charging them rent, because if you are, those days would count as rental days for tax purposes. If it's truly free family use, then it counts as personal use and reduces your deductible percentage. One more tip: take photos of the space in its rental-ready condition and keep receipts for any improvements or furnishings you buy specifically for the rental. These can help establish your basis for depreciation calculations.

This thread has been incredibly helpful! I'm dealing with a similar situation where my wife and I own our primary residence plus two adjacent lots that we've been using as extended yard space for the past 12 years. One lot has our pool and patio area, the other is mostly wooded but we use it for hiking trails and our kids built a treehouse there. Based on everything discussed here, it sounds like both lots should qualify for the capital gains exclusion along with our main house as long as we can document the residential use and sell within a reasonable timeframe. The advice about getting everything appraised together as one unit is brilliant - I'm definitely going to do that. One question I haven't seen addressed: does it matter that our lots are technically on separate parcels with separate property tax assessments? We receive three different tax bills each year, which makes me worry the IRS might view them as separate investment properties rather than part of our primary residence. Has anyone dealt with this situation where the adjacent land was on completely separate legal parcels? Also, for those who mentioned working with tax professionals specializing in real estate - any recommendations for finding qualified specialists? I want to make sure I get proper guidance before we start the selling process.

This has been such an informative discussion! I'm actually a tax preparer and wanted to add a few technical points that might help everyone here. First, regarding the separate parcel question - the IRS uses the "functional test" rather than just legal boundaries. As long as you can show the parcels were used together as your residence (which your pool, patio, trails, and treehouse clearly demonstrate), the separate tax assessments won't hurt you. In fact, I've seen cases where separate parcels actually helped establish clear ownership timelines. One thing I haven't seen mentioned is the importance of Form 8949 reporting when you do sell. You'll need to report each property separately on the form, but you can apply the Section 121 exclusion to the combined gain. I always recommend my clients include a statement explaining that the properties were used as an integrated primary residence - this proactive disclosure can prevent future IRS questions. Also, for those considering the timing of sales - while selling in the same tax year is cleanest, I've successfully handled cases where properties sold up to 18 months apart with proper documentation. The key is maintaining your narrative that they were always one residential unit, not separate investments. One last tip: if any of you have made capital improvements to the adjacent lots (landscaping, fencing, pool installation, etc.), make sure to include those in your cost basis calculations. These improvements can significantly reduce your capital gain and might even keep you under the $500K threshold if you're close to the limit.