I used both last year to compare them (before submitting with one). TurboTax was clearer about the 1098 boxes but charged extra for the mortgage deduction forms. TaxSlayer includes all that in their basic price, which is why I stuck with them.

Thanks for sharing your experience! Good to know about the pricing difference. I think I'll stick with TurboTax this year since I'm already familiar with it, but it's frustrating they charge extra for something TaxSlayer includes. Maybe I'll compare both again next year.

That's really helpful for going forward. But for this year, if I've already underpaid, is there any advantage to paying the remaining balance before I file versus at the time I file?

For your current situation, paying before you file won't eliminate the underpayment penalty that's already accrued, but it will stop additional interest from accruing. The Form 2210 penalty is calculated through April 15th (or your filing date if earlier). What you might want to check is if you qualify for any of the penalty exceptions. For example, if you paid at least 90% of the tax shown on your return for each quarter, or if your tax due is less than $1,000, you might avoid the penalty. Also, look at whether withholding might help - the IRS treats withholding as if it was paid evenly throughout the year, even if it wasn't.

The first-time penalty abatement usually doesn't apply to estimated tax penalties (Form 2210). It typically applies to failure-to-file and failure-to-pay penalties. Estimated tax penalties are considered different because they're not just about timely filing/payment but about making required payments throughout the year.

Thanks for sharing your experience! I hadn't even considered the QBI deduction. Do you remember how complicated the process was to switch from S to C? And now you're switching back? Did you use a specific service or accountant to help with the transition?

The conversion process itself wasn't too difficult - it's basically filing Form 8832 to elect C-corp status. The real complications came afterward with the new tax reporting requirements and accounting changes. I worked with my accountant who specializes in small business taxation. If you're considering a change, I'd definitely recommend working with a specialist rather than doing it yourself. There are timing considerations and potential tax implications that aren't obvious. For example, after you revoke S-corp status, you generally can't re-elect it for 5 years without IRS permission, which is why I'm having to go through a more complex process to switch back.

I did this calculation recently for a similar situation. Here's a simplified breakdown: S-corp: 60k business income passes through. Assuming a reasonable salary of 35k (subject to payroll taxes) and 25k as distribution (no SE tax). The 60k is taxed at personal rates, but with QBI deduction on qualified income. Approx total tax: $12-14k depending on deductions. C-corp: Corporation pays 21% on 60k = $12.6k. Then any money taken out as dividends gets taxed again at 15% (assuming qualified dividends). So if you took all remaining $47.4k as dividends, that's another $7.1k in tax. Total: $19.7k. This is simplified and excludes other factors, but illustrates why S-corps often work better for smaller businesses where owners need to take most profits out.

How do you get that verification letter? Is it something you can do online or do you have to call them?

You request it by submitting Form 4506-T to the IRS. Mark box 7 on the form which specifically requests the verification of non-filing letter. You can mail it in or fax it. Some schools will accept alternative documentation if you can't get the letter for some reason, like a signed statement certifying you didn't file. Check with your financial aid office about their specific requirements, as they can vary between schools.

Filing taxes has zero direct impact on your credit score. Credit bureaus don't even look at your tax returns. However, having tax returns can be helpful documentation when applying for larger loans like mortgages later on. Lenders sometimes want to see a history of tax returns, even for years with little/no income, to verify your financial history. But that's for major loans years down the road, not your regular credit score.

Yikes, that's terrible advice they gave you! You definitely need Schedule C for business income. I had a similar issue and ended up using FreeTaxUSA to file an amended return. I wouldn't trust Cash App to fix their own mistake.

Thanks for confirming what I suspected. I'll check out FreeTaxUSA for the amendment. I was worried about trying to fix it through Cash App since they clearly don't understand basic tax forms. Definitely learned my lesson about trying to save money on tax filing!

How do those crypto tax programs work? Do they connect to exchanges automatically or do you have to upload transactions manually?

Most of the good crypto tax programs can connect directly to exchanges through API connections, so you authorize them to pull your transaction history automatically. For exchanges that don't support direct connections, you can usually upload CSV files of your transaction history. They then calculate your cost basis, identify which transactions are taxable events, and generate a completed Form 8949 that you can either print or import into your tax software. The big advantage is having proper documentation of how your gains/losses were calculated if you ever get questioned by the IRS.