Do you meet with your CPA throughout the year or just at tax time? I'm wondering if there's value in quarterly check-ins or something.

I do both - a main consultation during tax prep season but also a mid-year check-in around June/July to make sure I'm on track with estimated payments and to discuss any new business developments or investments. The mid-year meeting is actually incredibly valuable because it gives me time to implement tax-saving strategies BEFORE year-end when many opportunities disappear. For example, last July we identified that I could purchase some needed business equipment before December and fully deduct it, saving me about $1,400 in taxes. Waiting until tax season in April would have been too late.

What kinds of deductions did you miss? I'm curious because I'm in a similar situation and wondering if I'm leaving money on the table.

That's an interesting idea! I'm not sure if I had any return of capital distributions. Is there a way to check that on the Webull platform? I'm still pretty new to investing and all these tax forms are confusing.

You can check by logging into your Webull account and going to the "Account" tab, then selecting "History" and filtering for "Dividends." Look for any entries labeled as "Return of Capital" or "ROC." If you see any of these, that's likely your culprit. Return of capital distributions are not technically dividends, but sometimes brokers report them incorrectly. If you find this is the case, you could try explaining this to TurboTax support as the reason for the discrepancy. Alternatively, you might need to manually override TurboTax's error check, though some tax software doesn't allow this without a paid upgrade to a premium version that allows manual entries.

Did Webull send the corrected form to the IRS too? I'm worried about making changes on my end but then having the IRS records show something different.

Does this apply to other tax forms too? We're about to submit for the Restaurant Revitalization Fund and I'm worried about similar delays.

Absolutely! This consistency rule applies to pretty much all tax forms and federal relief programs. For the Restaurant Revitalization Fund specifically, make sure your business name matches exactly what's on your business license, EIN documentation, and tax returns. I've seen applications get stuck in processing because the business applied as "Joe's Pizza" but their tax returns show "Joseph's Pizza LLC." The systems are often matching these entries automatically, and even minor differences can kick it out for manual review, which means significant delays.

You don't need to have fully shut down to qualify. There are two main ways to be eligible: 1) Your business operations were fully/partially suspended due to government orders limiting commerce, travel, or group meetings due to COVID-19, OR 2) You experienced a significant decline in gross receipts during a calendar quarter compared to 2019 (specific percentage requirements depend on which quarter you're claiming). Reduced hours can definitely qualify under the first test if they were the result of government restrictions. Document everything showing how the restrictions affected your operations!

Thank you for explaining! We definitely had reduced capacity requirements from our county health department that forced us to operate at 50% for several months. I'll gather all the official orders and our schedule changes to document this properly. I appreciate the clear explanation - our accountant was being super cautious about this claim since the IRS has been scrutinizing them closely.

I've heard of FreeTaxUSA but was worried about switching since I've used TurboTax for years. Does it handle importing 1099-B forms from Wealthfront or would I have to enter all those transactions manually? And is it actually reliable/secure? TurboTax's upselling is driving me nuts but I'm nervous about trying something new.

FreeTaxUSA doesn't have direct import from brokerages like Wealthfront, so you'd need to enter the transactions manually. However, if you don't have tons of transactions, it's not too bad - just time-consuming. The software is completely legitimate and secure - I've used it for three years now with no issues. It's actually owned by TaxHawk, which has been around for 20+ years. The interface isn't as pretty as TurboTax, but it's much more straightforward and has all the same features without the constant upselling. For Schedule D specifically, it's included in their base price (around $15 for federal filing) instead of requiring an expensive upgrade.

TurboTax is looking at the detailed transaction section, not just the summary fields. Even if the summary shows zeros, each individual buy/sell transaction needs to be reported on Schedule D. The summary fields OP mentioned (lines 8-11) are actually for futures/derivatives contracts, not regular stock transactions.

Does the QBI deduction apply even for side gig income? I thought that was only for like full businesses with employees and stuff.

The QBI deduction absolutely applies to side gig income! It's available for most self-employed individuals, regardless of whether you have employees or not. Even if you just drive for DoorDash or Uber on weekends, that income generally qualifies. There are some limitations and phase-outs at higher income levels (above $170,050 for single filers in 2024), but for most side-giggers, you can take the deduction without complications. It's essentially a free 20% deduction on your net business profit, which can significantly reduce your taxable income.

Yes, the IRS does sometimes grant a waiver for the underpayment penalty for first-time filers who weren't aware of the requirement to make estimated payments. This falls under their "first-time penalty abatement" policy. You generally need to have a clean compliance history for the past three years with no penalties. When you file, you can request this waiver by calling the IRS after you receive a penalty notice, or your tax preparation software might have an option to include a statement requesting the waiver due to reasonable cause. Just be honest about being new to self-employment and not understanding the estimated tax requirements previously.

Thank you everyone for such helpful advice! I've learned so much from all of your comments. I'll check out those resources mentioned and definitely start tracking my expenses better. I'm feeling way less panicked about tax season now!