If you're going to do this, be SUPER careful with documentation. My friend tried this with his lawn care business and got audited. The IRS disallowed all the deductions for his kids because he couldn't prove they actually did the work or that the pay was reasonable. Keep a timesheet for each kid with dates, hours worked, and duties performed. Pay them regularly (biweekly or monthly) not just one big payment at year end. Take pictures of them working if possible. And pay them a reasonable wage for their age and the work they're doing - don't pay your 10-year-old $50/hour for stuffing envelopes!

Just a heads up for anyone considering this - make sure you understand the state requirements too! I implemented this strategy with my home-based marketing consulting business last year, paying my 16 and 14-year-old kids for legitimate work (social media management, data entry, client research). While the federal tax benefits worked exactly as described, I learned the hard way that some states have additional requirements for employing minors, even in family businesses. In my state, I needed to get work permits for both kids and follow specific hour restrictions during school months. Also, don't forget about workers' compensation insurance requirements - some states require it even for family employees in certain business types. I had to adjust my business insurance policy to cover them. The tax savings were definitely worth it (saved about $3,200 in taxes last year), but factor in these additional compliance costs when you're calculating the benefit. Still came out way ahead, but wished I'd known about the extra requirements upfront!

Don't forget about local taxes! I'm in Pittsburgh and completely missed that I needed to pay quarterly estimated taxes to the city too. Got slapped with a penalty my first year of freelancing. Most tax software handles federal and state but often misses local obligations.

TurboTax and other tax software definitely handle both federal AND state taxes, but here's the catch - they don't automatically submit your quarterly estimated payments. They'll calculate what you should pay each quarter, but you still have to make those payments yourself throughout the year. At tax filing time, they'll prepare both your federal and state returns. But for quarterly estimated payments during the year, you need to handle those separately by submitting the appropriate forms to each tax authority (federal, state, local).

Can someone clarify the consequences if you're past the statute of limitations but you OWED money to the IRS? I'm in a similar situation where I made mistakes on older returns, but in my case I underreported some income. Getting nervous about what happens now.

I've been following this thread closely since I'm dealing with a similar situation with my 2019 and 2020 returns. One thing I want to add that hasn't been mentioned yet is the importance of checking if you qualify for any penalty relief programs. Even if you're within the statute of limitations and need to pay additional tax, the IRS has first-time penalty abatement and reasonable cause relief options that can waive penalties for honest mistakes. I discovered this when I had to amend my 2020 return - while I did owe additional tax, they waived all the penalties because I had a clean compliance history and could demonstrate reasonable cause for the error. Also, if anyone is still unsure about their specific situation, I'd recommend getting your tax transcripts from the IRS website first. They show exactly when your returns were filed and processed, which helps you calculate the exact statute of limitations dates for your amendments. It's free and gives you all the key dates you need to know.

This thread has been incredibly helpful! I'm also dealing with service dog expenses and had been putting off figuring out the tax implications. Reading through everyone's experiences, it sounds like the key things I need to focus on are: 1. Getting a detailed letter from my doctor explaining the medical necessity 2. Keeping meticulous records of all expenses, separating task-specific training from general care 3. Tracking mileage for all service dog-related trips 4. Calculating whether my total medical expenses (including the service dog costs) would make itemizing worthwhile One question I haven't seen addressed - does anyone know if there are any limits on how much you can deduct for service dog expenses specifically? I know medical expenses in general have the 7.5% AGI threshold, but are there any caps on the service animal portion specifically? Also, for those who have gone through audits or dealt with IRS questions about service dog deductions, what documentation proved most important? I want to make sure I'm keeping the right records from the start rather than scrambling later if questions come up.

Thank you all for this incredibly detailed discussion! As someone new to navigating service dog expenses, this has been a goldmine of information. I wanted to add one thing that my tax preparer emphasized - if you're claiming service dog expenses, make sure your dog is actually classified as a "service animal" under the ADA definition (trained to perform specific tasks for a disability) rather than an emotional support animal or therapy dog. The IRS follows the ADA definition pretty strictly for these deductions. Also, I learned that if you receive any reimbursements from insurance, disability benefits, or other sources for your service dog expenses, you need to subtract those amounts from what you can deduct. So if your health insurance covered part of the initial cost or training, that portion isn't deductible. One last tip - if you're unsure about the 7.5% AGI threshold calculation or whether itemizing makes sense, many tax software programs will automatically calculate both scenarios and tell you which saves more money. Sometimes it's worth doing a quick run-through even if you think the standard deduction will be better, just to be sure you're not missing out on savings. The documentation requirements seem strict but totally manageable if you stay organized from the start. Thanks again everyone for sharing your experiences!

Maxwell, you definitely need to report this $20K sale on your tax return. Since it's a collectible (baseball cards), any gain will be taxed as a collectible capital gain, which has a maximum rate of 28% - higher than regular capital gains. The tricky part is determining your "basis" in the cards since you don't have receipts. If you inherited them from your grandfather after he passed away, your basis would be their fair market value on the date of his death (called "stepped-up basis"). If he gave them to you while alive, your basis would be what he originally paid for them. Since you don't have documentation, you'll need to research what similar cards were selling for during the relevant time period. Look at price guides, auction records, or consult with a sports memorabilia appraiser. The IRS expects a "good faith" estimate when original records aren't available. Report the sale on Schedule D of your tax return. Even without a 1099 from the auction house, you're still required to report it - the IRS can potentially discover large bank deposits through other means. Better to be proactive and report it correctly than risk issues later.

Just want to add one important detail that hasn't been mentioned yet - the timing of when you sell matters for tax purposes. Since you've held these cards for years, any gain would qualify as long-term capital gains, which is good news even though collectibles have that higher 28% maximum rate. Also, keep detailed records of the auction house's commission and any other selling expenses (insurance, shipping, etc.) because these costs can be deducted from your sale proceeds when calculating your actual gain. So if you received $20K but paid $2K in fees, your actual proceeds for tax purposes would be $18K. One more thing - if this puts you in a higher tax bracket for the year, you might want to consider timing any other asset sales or tax strategies accordingly. The 28% collectibles rate only kicks in if you're already in higher tax brackets, so depending on your other income, you might pay less than that maximum rate.