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Another option that nobody has mentioned yet is to check if your brokerage offers basis reconstruction services. Fidelity helped me with a similar inheritance issue by researching historical prices based on the date of death. You'll need to provide documentation like the death certificate and proof of the trust distribution, but they can often do the calculation for you. There might be a fee, but in my case it was worth it for the peace of mind.
Liam McGuire
ā¢What if my brokerage is a smaller one that doesn't offer those kinds of services? I'm with a regional firm that's not as full-service as Fidelity or Schwab.
If you're with a smaller brokerage, you still have options. Even if they don't offer formal basis reconstruction services, their customer service might still be able to help you identify the share price on the date of death. If that doesn't work, you can also use resources like Yahoo Finance or Morningstar to look up historical prices for most mutual funds. Just search for SSHFX and find the historical price data for your uncle's date of death. Document how you determined the value (take screenshots), and keep that with your tax records.
Amara Eze
Have you considered using the alternative valuation date? IRS rules allow the executor to choose either the date of death OR 6 months after for valuation purposes. Might be worth checking which value was lower if youre trying to minimize capital gains taxes when you sell.
This is actually a really good point. The executor had to choose one valuation method for ALL assets in the estate though - they couldn't cherry pick different dates for different assets. So you might want to check what method was used on the estate tax return if one was filed.
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One thing nobody's mentioned yet - you should check if your employer at least withheld the correct federal income tax. Sometimes when they mess up state withholding, they screw up federal too. If they did withhold federal correctly, you might be able to apply some of your federal refund (if you're getting one) toward your state tax bill. Not all states allow this, but worth looking into. Also, make sure you keep all documentation showing your employer didn't withhold properly. If you end up getting hit with penalties, having this paper trail could help you get them reduced.
How would you even check if federal withholding was done correctly? I'm looking at my W-2 and box 2 has federal income tax withheld, but I have no idea if it's the right amount.
You can do a quick check by comparing what was withheld to roughly 12-22% of your income (depending on your tax bracket). But the more accurate way is to run your numbers through a tax calculator or software. Just input your total income, filing status, and deductions - then compare the "federal tax liability" it calculates against what was actually withheld on your W-2. If they're roughly in the same ballpark (within a few hundred dollars), then your federal withholding was probably done correctly. If the withholding is significantly less than your expected liability, then you've got problems on both federal and state levels, which is a much bigger issue.
Has anyone successfully sued their employer for failing to withhold state taxes? My cousin is going through this exact situation and is considering small claims court for the penalties and interest he's being charged.
Ethan Wilson
ā¢I looked into this when it happened to me. You probably can sue, but you'd need to prove they were negligent rather than it being a misunderstanding or paperwork error. Did your cousin explicitly fill out state tax withholding forms that were ignored?
He says he definitely filled out all the standard new hire paperwork including state tax forms. He even has copies that he saved. The company apparently just... didn't process them correctly? Or ignored them? Either way they admitted it was their mistake but are refusing to cover any of the penalties.
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Eve Freeman
DoorDash driver here for 3 years. The tax situation isn't as scary as people make it sound if you're organized. My advice: 1. Get a mileage tracking app RIGHT NOW (I use Stride) 2. Save 25-30% of everything you make 3. Take pictures of all receipts for hot bags, phone mounts, etc 4. Pay quarterly taxes if you make more than a few thousand Also, your car maintenance costs more than you think! That depreciation hits hard after a year or two of delivery driving.
Does the 25-30% include state taxes too or just federal? I'm trying to figure out exactly how much to set aside each week.
Eve Freeman
ā¢That percentage includes both federal and state taxes for most situations. If you're in a high-tax state like California or New York, you might want to bump it up to 30-35%. I'm in a medium-tax state and 28% has covered me completely. The exact amount depends on your overall income level and tax bracket when combined with any other jobs you have.
Caden Turner
Do any of you guys use TurboTax for your delivery gig taxes? Or is there a better option for self-employed people? This will be my first year doing DoorDash and I'm worried about messing it up.
Sunny Wang
ā¢I've used both TurboTax Self-Employed and FreeTaxUSA for my delivery gig taxes. TurboTax is more user-friendly and asks specific questions about delivery driving, but it's expensive (around $120-150 for federal and state with self-employment). FreeTaxUSA handles 1099 income well too and costs way less (about $15 for state, federal is free), but you need to know which forms to fill out yourself.
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Don't overlook local resources! Many cities have Small Business Development Centers that offer free or very low-cost accounting setup help. I got free QuickBooks training through mine last year. They also connected me with a retired accountant who volunteers to help new businesses set up their books properly.
Where would I find these centers? Is there a website or something to locate the one nearest to me? This sounds perfect for my budget right now.
You can find your local Small Business Development Center through the SBA website - just search "SBDC near me" and it should pop up. They're usually connected to local colleges or economic development agencies. Most offer free initial consultations where they'll assess your specific needs and then connect you with the right resources. Ask specifically about their accounting workshops - many run monthly QuickBooks or general bookkeeping classes designed for absolute beginners. The SCORE program (also through SBA) can match you with a retired accountant or financial professional who volunteers as a mentor.
Justin Trejo
I'm going against the grain here, but I think paying for a professional bookkeeper from day one is worth every penny. I tried doing it myself and ended up with such a mess that it cost me $2,700 to have an accountant fix everything at tax time. Now I pay $275/month for a bookkeeper who handles everything. She catches potential issues before they become problems and actually helped me identify several tax saving opportunities I never would have known about. Plus the time I save not dealing with receipts and categorizing transactions is time I can spend actually making money in my business.
Alana Willis
ā¢$275 monthly seems steep for a startup though... how many transactions do you have? And did you find someone local or use an online service?
James Johnson
One thing nobody mentioned yet - I always run my info through two different tax software programs and compare the results! I use FreeTaxUSA and then also input everything into TaxAct (or sometimes TurboTax if I can find a free version). If both software packages come up with the same refund/amount owed, I'm much more confident everything is correct. When they don't match, it helps me track down where the discrepancy is happening, which usually reveals an error in how I entered something. It takes extra time but gives me peace of mind, especially since different software sometimes asks questions in different ways that make me realize I misunderstood something.
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Ryder Ross
ā¢That's a really smart idea! Does FreeTaxUSA let you go through the whole process without paying? I know they charge for state filing, but do they let you see your final federal numbers before submitting payment? And have you ever found significant differences between the two calculations?
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James Johnson
ā¢FreeTaxUSA lets you go through the entire process and see your completed federal return for free - you only pay when you actually file. So you can definitely see your final numbers before deciding to submit. And yes, I've caught some pretty significant differences! Last year, there was a $1,200 difference between FreeTaxUSA and TurboTax on my refund. Turned out I had accidentally entered a 1099-MISC as a 1099-NEC in one of the programs which changed how the income was classified. Another time, I discovered I had incorrectly answered a question about qualified business income in one software but not the other. The cross-checking has definitely saved me from some big mistakes.
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Sophia Rodriguez
For us regular people with normal jobs and no fancy investments or rental properties, FreeTaxUSA is pretty foolproof. I've used it for 5 years now without any issues. My main tip is to compare this year's return to last year's. If there are big differences in adjusted gross income, total tax, or refund amount that don't match up with life changes you've had (new job, bought house, had baby, etc), that's a red flag to investigate. Most years your tax situation doesn't change dramatically unless something major happened in your life.
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Mia Green
ā¢This is great advice! I also recommend checking if your state tax refund/amount owed seems reasonable compared to your federal. They shouldn't be wildly different proportionately unless you live in a state with unusual tax situations. If federal shows a big refund but state shows you owing a ton, that could indicate something's wrong.
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