Thanks for the cost breakdown! That's super helpful. Do most of these professionals offer free consultations? I'd like to chat with a few before deciding.

Most reputable tax professionals do offer free initial consultations, usually lasting 15-30 minutes. This gives you a chance to explain your situation and see if they're a good fit, while they can give you a more accurate price estimate based on your specific needs. When you schedule these consultations, come prepared with a list of questions about their experience with multi-state taxation and small business equipment deductions. Also ask about their communication style and availability throughout the year - you want someone who's accessible for questions, not just at tax time. The right professional should feel like a partner in your business, not just a once-a-year service.

I second this! I use FreshBooks for my small business and it makes everything so much cleaner. I upload receipts throughout the year and when tax time comes, I just export everything and send to my EA. She charges me less because the data is already organized.

Thanks for explaining this! Do you think I should go back and amend my previous returns to add this penalty, or just start including it going forward now that I know?

I generally wouldn't recommend amending prior returns just to add an estimated tax penalty if the IRS hasn't noticed it. The statute of limitations for most issues is 3 years from filing, so older returns are likely closed anyway. Going forward, your best approach would be working with your accountant to either increase your withholding at your job (if you have W-2 income) or make quarterly estimated payments if you have significant 1099 income. Proper planning eliminates the penalty entirely, which is better than calculating it correctly! The penalty is meant to incentivize paying throughout the year rather than all at filing time.

Which tax software do you think handles this the best? I'm thinking of switching from FreeTaxUSA after reading this thread!

This is a great point! I've always found the "don't give the government an interest-free loan" advice to be overblown. With today's savings account rates, the interest you'd earn on that money throughout the year is minimal compared to the stress of potentially owing at tax time. For most W-2 workers, a small refund is actually good peace of mind.

Exactly! I calculated it out and even with a $2,400 refund (which is what I typically get), at 4% interest I'm only "losing" about $50-60 over the course of a year. That's well worth the peace of mind of not having to worry about owing money. Plus, I've gotten much better at immediately putting my refund into my Roth IRA each year so it starts working for me right away rather than getting spent.

Is there an income threshold where this starts to happen? My partner and I both make around $85k and are thinking about getting married next year. Would we be affected by this?

I've never heard of the Voluntary Disclosure Practice before. Is that different from the regular process of just filing late returns? Would I need to do anything special to qualify for that? For records, I have some bank statements showing cash deposits, and I've kept rough notes about my hours and pay rates over the years in various notebooks. Nothing official from the employer though. Would bank statements be enough to show the IRS what I earned?

The Voluntary Disclosure Practice is more formal than just filing late returns. It involves coming forward to the IRS before they discover the non-compliance, providing complete and truthful disclosure, and cooperating with the IRS to determine the correct tax liability. While it doesn't guarantee immunity from prosecution, historically it has significantly reduced the likelihood of criminal charges in cases of willful non-compliance. Your bank statements showing cash deposits will be extremely helpful. Combined with your notes about hours and pay rates, you actually have more documentation than many people in similar situations. The IRS understands that reconstructing income from years ago is difficult, especially with cash payments. They generally accept reasonable reconstructions based on the best available information. Make sure to be consistent and realistic with your income estimates - sudden unexplained variations might raise questions.

This is actually a really good point. I worked as a volunteer tax preparer, and many people don't realize that the EITC can result in substantial refunds for lower-income workers. If your annual income was under about $60,000 (varies by year and filing status), it's definitely worth looking into.

Thanks! Is there any difference feature-wise between the download version and online version if I go with Deluxe? Also, do you know if the download version includes a state filing or is that extra?

The download version and online version have essentially the same features for each tier, but the pricing structure is different. The download is a one-time purchase that you install on your computer, while the online version is a subscription service. Most people find the online version more convenient, but the download can be cheaper. State filing is almost always an additional cost regardless of which version you choose. The download versions typically charge around $40 per state, which is separate from the federal filing cost. Some retailers occasionally offer bundle deals that include one state filing, but that's not common - always check the packaging details to confirm what's included.

I would second this. Premier is only about $20-30 more than Deluxe and well worth it if you have investments. I've used it for years and the investment import feature works much better with Premier than with Deluxe.

Thanks for the tip! Guess I'll go with Premier to be safe. I do have some crypto I forgot to mention, plus stocks across three different platforms. Don't want to get stuck with upgrade fees at the end.