Something to consider - if your mom donates some of the less valuable items to charity instead of selling them, she might be able to claim a charitable deduction for the fair market value. Could be worth it if some items have sentimental value to others but aren't worth much financially to your family.

I went through something very similar when my grandfather passed and left behind a huge collection of vintage postcards and military memorabilia. One thing I learned that might help - keep detailed records of everything you research for values, even if you don't sell certain items right away. Take photos of the items with any identifying marks, serial numbers, or condition details. Save screenshots of comparable sales from eBay "sold listings" or auction sites with dates. This documentation becomes crucial if you sell items later or if the IRS ever questions your valuations. Also, consider selling higher-value items in different tax years if it makes sense for your mom's overall tax situation. Since each sale is a separate taxable event, spreading them out might help manage the tax impact, especially with that higher collectibles rate that Sean mentioned. The most important thing is getting that fair market value established at the time of your father's passing - everything else flows from there. Sorry for your loss, and I hope this helps make the process a bit easier for your family.

don't stress too much. I had about $35k in doordash income from 2021 I never reported and got hit with a big bill too. If u file now and apply for a payment plan the irs is usually pretty reasonable. I'm paying like $180/month which isn't too bad. Just make sure to file 2023 taxes on time so u don't dig the hole deeper!!!

I went through something very similar with my 2022 gig work taxes! That $10,400 estimate actually sounds pretty accurate unfortunately - self-employment tax alone is brutal at 15.3% on your net earnings, plus regular income tax on top of that. The penalties and interest really add up fast too. Here's what saved me: I gathered EVERY possible business expense I could find. Phone bills, car maintenance, gas receipts, even cleaning supplies for my car. But the biggest game changer was mileage - if you drove for deliveries, you can deduct 58.5 cents per mile for 2022. Even if you didn't track it perfectly, you can estimate based on your delivery patterns and the IRS accepts reasonable reconstructions. Also definitely look into that first-time penalty abatement others mentioned. I got about $2,800 in penalties waived just by calling and explaining it was my first time missing a filing deadline. The key is to file first and get on a payment plan, then request the abatement. Don't panic - the IRS wants their money but they're surprisingly willing to work with you if you're proactive about fixing it!

One approach my spouse and I use is to just slightly overwithhold by adding an extra fixed amount on line 4(c) of both our W-4s. We each add $25 per paycheck. By the end of the year, that's an extra $1300 withheld between us (we're both paid biweekly), which has always covered any surprise tax issues from our investments or side hustles.

Congratulations on getting married! As someone who went through this same situation a couple years ago, I'd definitely recommend starting with the IRS Tax Withholding Estimator that Ezra mentioned. It's free and gives you personalized recommendations. One thing I learned the hard way - don't just guess or use rules of thumb when your incomes are different like yours are. My husband and I initially just both checked the Step 2(c) box thinking that would be enough, but we ended up owing about $600 because we didn't account for some other factors properly. The estimator will ask for your pay stubs, expected annual income, filing status (married filing jointly), and any deductions you plan to take. It then gives you specific instructions for each of your W-4 forms. Since you're planning to file jointly and have that 30% income difference, it's really worth the 15 minutes to get it right rather than guessing and potentially owing at tax time. Also, remember you can always adjust your W-4s mid-year if your situation changes or if you find you're withholding too much or too little based on your paychecks!

Just want to add a data point - I had a similar issue and it turned out I wasn't eligible for APTC for one month due to having access to employer coverage that month (even though I didn't take it). The marketplace still paid APTC to my insurer but left Column B blank. When I called, they told me to use the SLCSP calculator tool to determine the correct amount for Column B, rather than leaving it as zero. Apparently a zero really isn't valid there on the 8962 form.

I had this exact same issue last year! Your tax software is correct to flag the $0 in Column B - it's actually not a valid entry on Form 8962 when you've received advance premium tax credits. Here's what's likely happening: The marketplace made an error on your 1095-A. Column B (SLCSP) is essential for calculating your premium tax credit eligibility, and it should never be blank or zero when you received APTC payments (Column C has a value). My recommendation is to use the SLCSP lookup tool on Healthcare.gov to find the correct amount for your zip code, family size, and coverage period for April. You'll need this information: your county, number of people covered, and their ages during that month. The tool will give you the official SLCSP amount that should have been in Column B. Once you have the correct SLCSP amount, enter it on your Form 8962 instead of the $0.01 workaround. This will give you an accurate premium tax credit calculation. You don't necessarily need to wait for a corrected 1095-A if you can verify the correct SLCSP amount yourself using the official tool. Just make sure to keep documentation of where you got the SLCSP figure in case the IRS has questions later.

Has anyone mentioned the potential for a tax-free reorganization under Section 368? I went through something similar with commercial properties in an S-corp and we managed to do a division into separate entities without triggering immediate tax liability. It was complex and required careful planning, but saved us a fortune.

This is exactly the kind of complex situation that requires specialized expertise beyond typical tax preparation. I've seen similar cases where families get trapped with appreciated assets in S-corps, and unfortunately there's no one-size-fits-all solution. One option you might not have explored yet is a charitable remainder trust (CRT) if you're charitably inclined. You could contribute some of the S-corp shares to a CRT, which would then sell the properties without immediate tax consequences to you, and you'd receive an income stream for life. This works especially well if you don't need all the property value immediately. Another consideration is whether any of the rental properties could qualify for opportunity zone deferrals if you're planning to reinvest. The timing with your father's passing might create some unique planning opportunities. Have you gotten a current appraisal on all four properties? Market conditions have changed significantly, and knowing exact current values versus basis will help determine which strategies make the most financial sense. Also, consider whether keeping one or two properties in the S-corp while extracting others might be a hybrid approach worth exploring. The key is running detailed projections on each option - sometimes paying the tax hit upfront is actually better than the ongoing complications and limitations of keeping everything in the S-corp structure.