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One thing nobody's mentioned yet - your mother-in-law's final tax return! Don't forget you need to file her personal income tax return for the partial year up until her date of death. This is separate from any estate tax returns. Also, depending on your state, there might be state inheritance taxes even if you're below the federal estate tax threshold. For example, Pennsylvania has an inheritance tax that kicks in at much lower values than the federal tax.
What about medical expenses she had before passing? Can those be deducted on her final return? My family member had nearly $30k in out-of-pocket medical costs in their final months.
Yes, medical expenses can be deducted on the final tax return, and they're subject to more favorable rules in this situation. Medical expenses paid by the estate within one year of death can be treated as if they were paid at the time of death, and can be deducted on the final income tax return. The threshold for deducting medical expenses is typically 7.5% of adjusted gross income, but given the potentially large expenses in a final illness, it's quite possible you'll exceed that threshold and be able to take a substantial deduction.
From my experience with my parents' estate, document EVERYTHING. Keep detailed records of every penny spent on funeral costs, home maintenance, attorney fees, etc. These are typically expenses of the estate and reduce the taxable amount. Also, be careful about who serves as the executor/trustee. It's a lot of work and can create resentment if one person is doing everything. Our family ended up hiring a neutral third party to serve as executor after siblings couldn't agree, and it was worth every penny to preserve relationships.
How much did it cost to hire a third-party executor? We're considering this option because tensions are already high.
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I've been doing taxes for friends with crypto for a few years. One thing nobody mentioned is that transfers between wallets (like from Coinbase to your personal wallet) aren't taxable events - but transfers to a casino ARE considered disposals because you're effectively "selling" your crypto to the casino for gambling credits. That's an important distinction. Also, offshore casinos are a gray area. They technically should report large winnings to the IRS, but many don't. That doesn't absolve you from reporting, though - the responsibility is still on you as the taxpayer.
So given my specific situation - if I buy Bitcoin and immediately transfer to a casino, I'd report it on Form 8949 as a purchase and sale with zero gain/loss? And then the gambling part would be totally separate on different forms?
That's exactly right. You'd show the Bitcoin purchase and disposal on Form 8949 with the same amounts (so zero gain/loss). Then separately, you'd report any gambling winnings on Schedule 1 as "Other Income." If you itemize deductions rather than taking the standard deduction, you could potentially deduct gambling losses (up to the amount of your winnings) on Schedule A. But only if your total itemized deductions exceed the standard deduction, which is $13,850 for single filers in 2023.
Has anyone dealt with the record-keeping nightmare for this? My gambling site only keeps 3 months of history and I've been doing this all year. Should I be taking screenshots of every session? What counts as adequate proof for the IRS?
I use a spreadsheet to track everything - date, amount of crypto purchased, transfer to site, gambling sessions with wins/losses. I also take screenshots of big wins and all withdrawals. For the actual crypto purchases, your exchange should have all that history available to download.
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Make sure you're looking at ALL your tax credits too, not just EITC. With two dependents, you should be getting Child Tax Credit which is worth up to $2,000 per qualifying child. The lookback provision doesn't apply to CTC, but with your income level, you might qualify for Additional Child Tax Credit which is refundable. Also check if you qualify for the Child and Dependent Care Credit if you paid for childcare so you could work or look for work.
Thanks for mentioning this! I didn't think about the Additional Child Tax Credit. Do you know if unemployment income counts toward eligibility for that? And does the Child and Dependent Care Credit apply if the childcare was only for part of the year (Jan-Mar before I lost my job)?
Unemployment income does count toward eligibility for the Additional Child Tax Credit, which is good news in your case. The ACTC looks at your total income, not just earned income like the EITC does, so your unemployment benefits will help you qualify. For the Child and Dependent Care Credit, you can absolutely claim it for just part of the year. You can claim expenses you paid for childcare during the months you were working (January-March). Even though it was only a few months, every bit helps when it comes to maximizing your refund.
Has anyone actually verified if this lookback provision is still available for 2023 taxes (filing in 2024)? I know it was definitely a thing during COVID, but I thought some of these special provisions expired.
I just checked the IRS website and unfortunately I think the EITC lookback provision expired. It was specifically extended for 2021 taxes (filed in 2022) but I don't see anything about it being available for 2023 tax returns. That might explain why your refund is lower.
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One important thing nobody has mentioned is that you don't have to choose between W-2 and 1099/LLC forever. Many contractors cycle between different work arrangements. I personally keep my LLC active even during periods when I take W-2 positions because it allows me to still do side gigs under the LLC umbrella. The annual fees to maintain an LLC are typically small ($50-$300 depending on your state) compared to the liability protection and professional appearance it provides. Also, don't overlook the business expenses you can deduct that you couldn't as a W-2: professional development, conferences, software subscriptions, a portion of your cell phone, business travel, etc. These deductions often offset much of the additional self-employment tax burden.
That's a good point about keeping the LLC active. My state charges $125 annually to maintain it. Do you track W-2 income and LLC income separately? And how do you handle retirement contributions when you have both types of income?
Yes, you absolutely need to track W-2 income and LLC income separately. I keep separate bank accounts and credit cards for business expenses to make this clean and audit-proof. For retirement contributions with both income types, it gets interesting and potentially advantageous. If your W-2 employer offers a 401k, you can max that out ($22,500 in 2023 plus catch-up if eligible), AND you can still contribute to a Solo 401k through your LLC as the "employer" portion. You can't double-dip on the employee contribution, but the employer contribution is based on your LLC profit. This lets you potentially put away significantly more for retirement than you could with just W-2 employment. Just make sure you're working with a tax professional who understands these nuances, particularly if you're juggling both types of income. These hybrid situations can be tax-advantageous but require careful documentation.
Honestly the biggest mistake people make with LLCs is not tracking expenses properly. Get accounting software ASAP! I use QuickBooks Self-Employed ($15/month) and it automatically categorizes most transactions and calculates my quarterly tax estimates. For retirement, a Solo 401k is WAY better than a SEP IRA in most cases because you can contribute more at lower income levels. You can put away up to $22,500 as the "employee" PLUS ~20% of your net business income as the "employer" in 2023. And don't forget about health insurance! Your health insurance premiums are deductible above the line as self-employed, which is huge.
Is there a cheaper alternative to QuickBooks? $15/month seems steep when I'm just starting out with a small side business.
Micah Trail
3 Don't stress too much about criminal charges. The IRS is mostly concerned with collecting taxes, not prosecuting people who are trying to fix their mistakes. Criminal charges are typically reserved for people who are deliberately committing fraud or trying to evade taxes, not those who fell behind and are now trying to catch up. I was in a similar situation about 5 years ago (hadn't filed for 4 years) and just worked through it systematically. The penalties weren't as bad as I expected, and for one year I actually got a refund! The peace of mind from getting everything sorted out was absolutely worth it.
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Micah Trail
•16 Did you file yourself or use a professional? I'm trying to decide if I need to hire someone or if I can handle this on my own with tax software.
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Micah Trail
•3 I started with tax software for the most recent year I hadn't filed, since that was the simplest one. I was able to handle it myself pretty easily since I just had W-2 income like you do. For the older years, I ended up using a tax preparer because my situation got more complicated (had some 1099 income and moved states). If your tax situation is straightforward with just W-2 income, you can absolutely do this yourself with tax software. Many of the major tax software companies offer versions for prior years. Just make sure you're filing paper returns for prior years since electronic filing is usually only available for the current tax year.
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Micah Trail
5 Just wanted to add that if you do end up owing money to the IRS, don't panic about paying it all at once. The IRS is pretty reasonable about setting up payment plans. I owed about $7,500 after not filing for a couple years, and they let me set up a monthly payment plan of $250. The most important thing is to file all the returns, even if you can't pay right away. The penalty for not filing (failure-to-file penalty) is much higher than the penalty for not paying (failure-to-pay penalty).
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Micah Trail
•20 Is there an application process for the payment plan? And do they charge interest while you're paying it off?
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