Thanks for mentioning Opportunity Zones. I've heard of them but don't really understand how they work. Do I have to invest the exact amount of my gains, or can I do partial? And is there a time limit after selling my stocks to invest in an OZ?

You need to invest your capital gains (not necessarily the entire proceeds from your sale) into a Qualified Opportunity Fund within 180 days of realizing the gain. You can definitely do partial investments - any portion of your gains that you invest will get the tax deferral. The main benefits are: 1) You defer paying taxes on your original stock gains until 2026, 2) If you hold the OZ investment for 5+ years, you get a 10% reduction on those original deferred taxes, and 3) If you hold the OZ investment for 10+ years, any new gains from the OZ investment itself are completely tax-free. It's complex but can be very advantageous if real estate investing aligns with your goals.

Yes! I trade in my Roth and it's awesome for tax-free growth. But there are limits - you can only contribute $7,000/year for 2025 if you're under 50, and there are income phaseouts that start around $146,000 for single filers. Also, you can't touch the earnings without penalties until 59½ in most cases.

I actually do have a Roth IRA but haven't been very active with it. I'm contributing the max already, but never thought about doing my more active trading in there instead of my regular brokerage account. Might be a good strategy for next year to avoid this tax situation altogether.

Thank you, that's actually really helpful. It never occurred to me that Dad might have had accounts we didn't know about. He wasn't exactly organized with his paperwork in his final years. I'm going to request that transcript right away. Has anyone had experience with requesting an extension? Is it a complicated process or pretty straightforward?

Requesting an extension is very straightforward. When you call the IRS (using the number on your notice), simply tell them you need additional time to gather documentation to respond to the notice. They'll typically grant a 30-day extension verbally right then and there. Be sure to make note of the date of your call, the name of the representative you spoke with, and the new deadline date they provide. This information can be important if there's ever any question about whether you requested the extension.

This happened to my family too! The bank issued a 1099-INT to the estate rather than to my mom's final tax return. Such a headache to resolve. Does the IRS notice show an EIN that doesn't look familiar?

I hadn't considered bankruptcy yet. That feels like a last resort to me, especially since I'm trying to restart my business. Would the 2021 crypto tax debt even qualify since it's more recent? And wouldn't bankruptcy make it impossible to get business loans or credit in the future?

You're right to be cautious about bankruptcy. The 2021 crypto debt wouldn't qualify yet - tax debts must generally be from returns due at least 3 years before filing bankruptcy. So that major portion of your debt wouldn't be dischargeable right now. Bankruptcy does seriously impact your credit and ability to get business financing - typically stays on your credit report for 7-10 years. Since you're restarting your business, this could definitely create significant obstacles. Many business loans, commercial leases, and vendor credit arrangements check bankruptcy history specifically. I'd exhaust all options with penalty abatement and payment plans first before considering this route.

This is really important advice! I made a partial payment on my tax debt without understanding the implications and it reset the 10-year collection statute. Definitely talk to your LITC advisor first.

Be really careful with the big chains! I used H&R Block for my LLC last year and the preparer missed several deductions that I later realized I was eligible for. When I went back they wanted to charge me $250 just to file an amendment. Ended up being a huge hassle.

That's a fair point about inconsistent quality. I've had good experiences by specifically requesting their senior tax pros who have experience with small businesses, but you definitely need to be proactive about it. One approach that works well is to call ahead and ask about their staff's experience with your specific business type before booking. The franchise locations (rather than corporate-owned) often have more experienced preparers who've been working with the local business community for years. But you're right that it can be hit or miss if you don't do your homework first.

That's a really good point I hadn't considered. Did you find your CPA through a referral or just searching online? And did they identify themselves as specializing in tax savings specifically?

I found mine through a business networking group in my area, which I highly recommend over random online searches. The best tax preparers often don't need to advertise much because they get most clients through referrals. When interviewing potential accountants, ask specifically about their approach to finding deductions and minimizing tax liability. A good one will immediately start asking you detailed questions about your business structure, expenses, and financial situation rather than just quoting you a price. Mine actually did a free review of my previous year's return during our consultation and pointed out several missed opportunities before I even hired him.

I hadn't considered Drake! Does it handle direct import from TradeLog or would I still need to use the PDF export method? I'm open to trying new software if it saves me from printing everything.

Drake doesn't have direct integration with TradeLog that I'm aware of, so you'd still need to use the PDF export method. The advantage is just that Drake can handle much larger PDFs without breaking them up. If you want direct integration, you might look at TaxACT Professional (different from the consumer version) which has more import options for investment data. It's more expensive but might be worth it for the convenience if you have hundreds of transactions every year.

This is a good suggestion. Another trick is to export as grayscale and lower the resolution. Most tax forms don't need color or high resolution. I got a 15mb file down to 2.8mb doing this.