Something else to consider - do either you or your sister plan to live in the house at all before selling? If one of you moved in and used it as your primary residence for at least 2 years, you might qualify for the Section 121 exclusion, which lets you exclude up to $250,000 of capital gain from your income ($500,000 for married couples filing jointly). It's a long-term strategy and might not be practical in your situation, but worth mentioning as it's one of the biggest tax breaks available for residential real estate.

I'm sorry for your loss. This is definitely a complex situation that requires careful handling. One important point that hasn't been fully addressed yet - you mentioned your sister is the executor of your father's estate. Since your father passed away in August (after the July quitclaim deed transfer), there may be some coordination needed between how this transfer is handled and the overall estate administration. The executor will need to include information about this quitclaim deed transfer in the estate tax return (Form 706, if required) and potentially amend any gift tax considerations. Make sure your sister is working with a qualified estate attorney or CPA who understands both the gift tax implications of the July transfer AND the estate tax implications following your father's death. Also, keep detailed records of all expenses related to maintaining, improving, or selling the property after you received it - these can potentially be added to your basis and reduce your capital gains when you do sell. Given the complexity and the significant tax implications involved, I'd strongly recommend getting professional advice from someone who specializes in estate and gift taxation rather than trying to navigate this alone.

Warning from someone who got audited: Make sure you keep DETAILED records of all business travel! The IRS specifically looks at travel deductions. For each trip, document: 1) business purpose 2) dates 3) who you met with 4) all receipts. I had a bunch of legitimate business travel but couldn't prove some of it during my audit and lost those deductions.

Great advice from everyone here! As someone who's been through the business travel deduction maze myself, I just want to emphasize a key point that might save some headaches: the "away from home overnight" rule. If your business trip requires you to sleep away from home (like Chloe's 3-day meeting example), then ALL your transportation costs are deductible - airfare both ways, airport parking, rental cars, the works. But if it's just a day trip where you return home the same day, you can still deduct transportation to temporary work locations, but the rules are slightly different. The IRS considers anything over 100 miles from your tax home as likely requiring overnight stay, which makes the deduction clearer. Also, keep receipts for everything over $75 - that's the IRS threshold where you need actual documentation rather than just logging the expense. For smaller amounts, a detailed log is usually sufficient.

I'm dealing with the exact same situation right now. When I entered both 1099-Rs in FreeTaxUSA, it seemed to handle them correctly. The one with code H didn't add anything to my taxable income, but it still showed up in the tax forms. Has anyone used H&R Block software for this situation? Wondering if different tax programs handle these Roth distribution codes differently.

I went through something very similar last year and can confirm what others have said - you absolutely need to report both 1099-Rs even though one might be completely non-taxable. The code H form for your $12,000 transfer is straightforward - that's a direct rollover between Roth IRAs which isn't taxable but must still be reported. The form without a distribution code for your $8,500 home purchase withdrawal is also likely non-taxable since first-time home buyer distributions from Roth IRAs are penalty-free (though there are some nuances about contributions vs. earnings). One thing to double-check: make sure the amounts on your 1099-Rs match what you actually received. I had an issue where my old broker issued a 1099-R for the gross amount transferred, but my new broker also issued one, creating a discrepancy I had to sort out. Most tax software will handle these correctly if you enter them exactly as shown on the forms, including all the codes. The key is being accurate with the distribution codes in Box 7 - that's what tells the IRS (and your tax software) how to treat each distribution.

This is a really complex situation that depends heavily on which depreciation method you've been using! Since you mentioned tracking mileage meticulously, I'm curious - have you been using the standard mileage deduction or actual expenses (including depreciation) for your current vehicle? If you've been using standard mileage, your tax situation when selling will be quite different from what some others have described. The standard mileage rate includes a depreciation component (around 27 cents per mile in recent years), so your adjusted basis would be your original cost minus the total depreciation embedded in all those standard mileage deductions over 6 years. However, if you've been claiming actual depreciation and the car is fully depreciated as you mentioned, then yes - you're looking at significant depreciation recapture taxed as ordinary income when you sell. For the new $38,000 vehicle, switching to actual expenses could be beneficial since you'd be able to claim bonus depreciation or Section 179 expensing. Just remember that once you switch to actual expenses for a vehicle, you can't go back to standard mileage for that same car. Given the amounts involved here, I'd strongly recommend consulting with a tax professional before making the purchase. The timing of when you sell the old car versus buy the new one, plus which depreciation method you choose going forward, could save or cost you thousands in taxes.

You're absolutely on the right track with your calculation! Yes, with standard mileage deduction over 6 years, your adjusted basis would be significantly higher than someone who fully depreciated their vehicle using actual expenses, which means a much smaller taxable gain. One additional consideration I'd mention - when you switch to actual expenses for your new vehicle, make sure you're prepared for the record-keeping requirements. You'll need to track not just mileage, but also maintenance, repairs, insurance, registration fees, and all other vehicle-related expenses. It's more work than standard mileage, but with a $38,000 vehicle and current bonus depreciation rules, the tax savings should make it worthwhile. Also, don't forget that your business use percentage (80% in your case) applies to all these deductions. So on that $38,000 vehicle, you'd be looking at bonus depreciation on about $30,400 of the purchase price, which could provide substantial first-year tax savings to offset your gain from the sale. The timing strategy others mentioned is spot-on too - selling early in the year and purchasing late in the year maximizes your depreciation deduction in the year of sale. Good luck with the upgrade!

As someone who's also adjusting to the U.S. tax system from abroad, I completely relate to your confusion! The unpredictability compared to other countries' systems is definitely jarring at first. From my experience and what I've learned here, Tuesday night into Wednesday morning (3-6am Eastern) is your most reliable window. I used to check randomly like you did and it was exhausting! Now I've settled into a routine: check Wednesday morning around 8am with my coffee, and if nothing's there, I check again Saturday morning. One thing that helped me understand the system better was realizing that the IRS processes returns in weekly batches tied to cycle codes, not continuously like many other tax systems. Once you get your first transcript update, you'll see your cycle code which will help you predict future updates more accurately. Don't feel bad about that 4am checking session last year - we've all been there! The key is working with the system's rhythm instead of against it. Your transcript will update when it updates, and stressing over the exact timing won't make it happen faster. Focus on the Wednesday morning checks and save yourself the lost sleep!

Coming from a different tax system myself, I totally understand the frustration with the unpredictable timing! The consensus here is spot-on - Tuesday night into Wednesday morning (3-6am Eastern) is definitely your best bet. What really helped me was shifting my mindset from "when will it update?" to "when should I check?" I now check Wednesday mornings around 7am, and if there's nothing new, I'll check again Saturday morning. This saves me from the constant refreshing cycle that was driving me crazy my first year. The IRS batch processing system is so different from what many of us are used to internationally. In my home country, tax updates were almost immediate, so waiting for these weekly cycles felt bizarre at first. But once you understand that it's not personal - it's just how their system works - it becomes much less stressful. Don't waste your sleep checking at 3am like some people do. The transcript will be there at 7am if it updated overnight, and you'll actually be rested enough to understand what you're looking at! Save your energy for interpreting all those transaction codes once your transcript finally appears.