Somewhat unrelated but if you do decide to claim those miles, make sure you're using the correct mileage rate! For 2024 tax year it's 67 cents per mile which is higher than previous years. Also, use a dedicated mileage tracking app that logs your location. The IRS has been getting stricter about documentation for mileage claims, especially for gig workers. I learned this the hard way when I got audited for my Uber driving miles last year.

I've been in a similar situation with my rideshare driving and learned a lot about this from experience. The key thing the IRS looks at is whether your trip would have happened anyway without the business purpose. Since you're visiting friends monthly regardless, those 150 miles each way are personal travel. However, you're absolutely right to track all the miles you drive while actually working in that city - those are 100% deductible business miles. Don't shortchange yourself there! One thing to consider: if you can show that you're strategically choosing to visit during peak earning times (like weekends or events) and you're making substantial income there, you might have a stronger case. But honestly, given that visiting friends is your primary reason, I'd stick with your conservative approach. The IRS has been cracking down on gig worker deductions lately, so it's better to be safe than sorry. Focus on maximizing your legitimate deductions (the actual delivery miles, phone bills, car maintenance) rather than pushing the envelope on questionable ones.

Just went through this exact situation last year. Here's something important - check if your tax software is correctly differentiating between "excess depreciation" and regular depreciation on Form 8829. Sometimes the software puts numbers in line 44 that include both. In my case, I had to look at line 42 from each year to get the actual depreciation amount. Line 44 was higher because it included some casualty losses. Make sure you're not overstating your recapture amount!

I went through this exact nightmare two years ago when we sold our house after running a consulting business from home for 6 years. The depreciation recapture hit us for about $18k that we weren't prepared for. A few critical things I learned the hard way: First, definitely look at Form 8829 line 42 (not just line 44) from each year - that's the actual depreciation amount. Line 44 can include other items that aren't subject to recapture. Second, even if you forgot to claim depreciation in some years, the IRS considers you "entitled to take it" so you may still owe recapture on the amount you should have claimed. The 25% recapture rate applies regardless of your regular tax bracket, which is why it creates such a big hit. And yes, it's completely separate from the $500k exclusion - that was the part that blindsided us. One thing that helped: if you improved the office space during those years (new flooring, electrical work, etc.), those improvements may reduce your recapture amount since they increase your basis. Make sure you account for any business-related improvements to the office area. Given the dollar amounts involved, it might be worth paying for a consultation with a different CPA who specializes in real estate transactions, even if it's just for a one-time review.

Derek, based on what you've described, it sounds like your entire pension distribution is taxable. When Box 2a is empty and Box 2b is checked for "taxable amount not determined," combined with $0 employee contributions shown on your 1099-R, this typically indicates that your employer funded the entire pension with pre-tax dollars. Code 7 just means it's a normal distribution - no early withdrawal penalties or special circumstances. The key factor here is that $0 in employee contributions. If you had contributed after-tax money to the pension during your employment, you'd be able to recover those contributions tax-free. But since there are no employee contributions listed, the IRS will treat the full amount as taxable ordinary income. I'd recommend double-checking with your former employer's HR or pension administrator to confirm your contribution history, but based on the 1099-R you received, you'll likely need to report the entire distribution as taxable income on your return. Make sure to set aside money for the tax liability if you haven't had taxes withheld from your pension payments.

I went through this exact same situation two years ago with my pension from a manufacturing company where I worked for 22 years. The 1099-R looked identical to what you're describing - empty Box 2a, Box 2b checked, and $0 employee contributions. After consulting with a tax professional and reviewing my old employment documents, we confirmed that the entire distribution was indeed taxable. The company had funded 100% of the pension with pre-tax dollars, so there was no tax-free portion to recover. One thing that helped me was requesting a "Summary Plan Description" from the pension administrator. This document clearly outlined how the plan was funded and confirmed that employees didn't make any after-tax contributions to this particular pension plan. It gave me the confidence I needed to report the full amount as taxable income. Since you mentioned you're currently working at a different company, just make sure you're prepared for the tax impact. Pension income can push you into a higher tax bracket, especially if you're still earning wages. I ended up increasing my quarterly estimated tax payments to avoid a big bill at filing time.

Does anyone know if there are exceptions to getting a 1099-S? I sold a small parcel last year and never got one either but my tax guy said it wasn't needed in my case.

Just to add some clarity on the timing - while title companies have until January 31st to send you the 1099-S, most reputable companies will get it to you much sooner, often within 30-60 days of closing. Since you mentioned it's been over three weeks, I'd definitely recommend reaching out to them now rather than waiting. When you contact them, have your settlement statement handy with the closing date and property address. They'll likely ask for this information to locate your file. Also double-check that they have your current mailing address - address mix-ups are surprisingly common and could explain the delay. Even without the 1099-S in hand, start gathering your other documents now: original purchase paperwork, records of any improvements you made to the land, and your closing/settlement statement from the recent sale. You'll need all of this to properly calculate your capital gains anyway, so getting organized early will save you stress later.

Looking at the 2023 tax year provisions, you should be aware that the Child Tax Credit is worth up to $2,000 per qualifying child under 17, with up to $1,600 being refundable (as the Additional Child Tax Credit). Even with zero income, you can receive this refundable portion. The filing deadline this year is April 15, 2024, so you still have time to file and claim these credits yourself. Your fiancé cannot claim the children unless you're legally married, as the IRS defines a step-parent relationship only through legal marriage. The biological parent with custody (you) has priority claim rights regardless of who provides financial support.

I've been following this thread and want to add something important that hasn't been fully addressed yet. Even though your fiancé can't directly claim your children as dependents, there's still a way for your household to maximize tax benefits while staying completely within IRS rules. Since you're the custodial parent, you should definitely file your own return and claim the kids - even with minimal income from gig work. Here's why this is actually beneficial: 1. You'll likely qualify for the full refundable Child Tax Credit ($1,600 per child under 17) 2. With gig work income, you might also qualify for the Earned Income Tax Credit 3. These are refundable credits, meaning you get money back even if you owe no taxes The key insight here is that it doesn't matter which person in your household files the return - the refund benefits your family either way. Your fiancé supporting you financially doesn't change who can legally claim the children, but it also doesn't reduce the tax benefits flowing to your household. One practical tip: make sure you file early in the season. If there's any confusion about who should claim the children, the IRS generally honors the first return filed with those dependents. This protects you from potential issues if the biological father changes his mind or files incorrectly.