I use Drake too and went with TheTaxBook last year. Found a good deal by buying during their summer sale. But honestly, I think the bigger question is whether you really need a physical book at all anymore? Drake has pretty decent built-in help, and I find myself using the IRS publications online more and more.

I've been using Drake for about 3 years now and went through this same decision last season. Ended up going with TheTaxBook after trying both, and I'm really glad I made the switch. The way TheTaxBook organizes information just flows better with how Drake presents forms and schedules. For discounts, I'd definitely recommend checking out professional associations like others mentioned, but also try reaching out to local tax preparer groups in your area. Our local AICPA chapter does a group buy every year that saves us about 25% off retail. You might also want to call TheTaxBook directly - I found their customer service much more helpful than CCH when I had questions about which edition would work best for my practice. One tip: if you do go with TheTaxBook, get the spiral-bound version if you're getting print. It lays flat much better when you're working at your computer with Drake open. Makes a big difference during busy season when you're constantly referencing it!

Has anyone used TurboTax for filing when they have an eBay 1099? I'm in the same boat and wondering if the free version can handle this or if I need to upgrade to the self-employed version?

I went through this exact situation last year and wanted to share what I learned! You absolutely need to file even if you sold everything at a loss - the IRS will assume that entire $6,800 is profit if you don't report it properly. Here's what worked for me: I created a simple spreadsheet listing each item I sold, what I originally paid for it, and what I sold it for. Even without receipts, you can use reasonable estimates based on what you remember paying or what similar items cost when you bought them. Bank statements, credit card records, or even photos with timestamps can help support your estimates. The key is reporting this on Schedule C to show your cost of goods sold. If you truly sold everything at a loss, you'll end up with zero taxable income from eBay, but you still need to file to prove this to the IRS. For software, I used FreeTaxUSA's Deluxe version (around $15) and it walked me through everything step by step. Much cheaper than TurboTax's self-employed version and just as good for this type of situation. The software will ask you simple questions about your eBay sales and generate the right forms automatically. Don't stress too much - this is actually pretty common now with the new 1099 reporting requirements. Just make sure you file something to avoid getting a scary notice from the IRS later!

Just wondering if anyone has tried Credit Karma Tax? I've been using it for the past two years. It doesn't have a fancy "find all deductions" feature, but it's FREE and does ask a pretty comprehensive set of questions. Found a few deductions I didn't know about last year.

As someone who's been doing my own taxes for over a decade, I can relate to this struggle! The frustrating thing is that you're absolutely right - there ARE tons of deductions buried in the tax code that most people never discover. I've found that the best approach is actually a combination of tools rather than hoping for one perfect app. I use TurboTax for the basics, then cross-reference with IRS Publication 17 (it's free online) which lists pretty much every individual deduction with examples. It's dry reading but worth it. Also, don't overlook state-specific deductions! Many apps focus on federal but miss local opportunities. For example, my state has deductions for energy-efficient home improvements that saved me $300 last year. The taxr.ai recommendation from Keith sounds promising though - might have to check that out before next tax season. An AI that actually cites tax code sections would be a game changer.

Did you submit your reasonable cause statement via certified mail with return receipt? This is crucial for dealing with the IRS, especially for something with potential large penalties like Form 3520. If you didn't, you have no proof they actually received your materials. I learned this the hard way when the IRS claimed they never received my response to a similar issue. Now I send everything certified and keep a copy of EVERYTHING. Its annoying but worth it.

I went through almost the exact same situation with Form 3520 penalties for educational gifts. After 9 months of silence, I finally got through to the IRS and learned that my case was actually resolved months earlier - they had accepted my reasonable cause statement but never sent confirmation due to what they called a "correspondence processing error." The key thing that helped me was getting my Statement of Account (different from regular transcripts) which showed the internal case activity. You can request this by calling and specifically asking for a "Statement of Account for Form 3520 submissions" - it shows processing codes that regular transcripts don't include. Also, I'd recommend documenting everything from this point forward. Create a timeline of all your submissions, the May 28th letter, and any attempts you've made to contact them. If you do end up needing to escalate to the Taxpayer Advocate Service, having this documentation ready will speed up the process significantly. The fact that you haven't received any penalty assessment notices after 10 months is actually encouraging - in my experience, the IRS is pretty quick to send penalty notices when they're rejecting reasonable cause statements.

Little-known fact: if you e-file, the IRS actually gets digital copies of your W-2s directly from your employer in most cases! That's why e-filing is less prone to these kinds of errors. The W-2 attachment requirement is mainly for paper filing. If you do need to paper file again, remember to sign in BLUE ink (makes it easier for them to identify original signatures vs photocopies) and attach all W-2s with paper clips, not staples.

One thing that helped me when I had a similar situation - make sure to double-check that all your W-2 information is entered correctly in TurboTax before you e-file. Even a small typo in the employer name or wage amounts can cause issues. Also, since you mentioned this is your first time filing independently, here's a helpful tip: after you e-file, you should get email confirmations from both the IRS (for federal) and Illinois (for state) within 24-48 hours confirming your returns were accepted. If you don't get those confirmations, log back into TurboTax to check the status. Don't stress too much about the delay - getting your return sent back actually happens to a lot of people, especially first-time filers. The important thing is you caught the mistakes and can fix them now!