Has anyone tried just using Google Drive or Dropbox instead of specialized tax document software? Seems like paying for fancy features might be overkill for a small practice?

As someone who recently went through this exact transition, I can't stress enough how much the right document management system will transform your practice. I was in your same situation last year - drowning in paper and basic cloud storage that was becoming a nightmare. One thing I wish I had considered earlier is the total cost of ownership beyond just the monthly subscription. Factor in training time, data migration, and potential productivity loss during the transition. I made the mistake of switching systems right before tax season and it was stressful, even though it worked out great in the long run. Also, whatever system you choose, make sure it has robust backup and disaster recovery features. I learned this the hard way when my old system had a sync issue that could have lost weeks of client uploads. Now I always ask about their backup protocols and how quickly they can restore data if something goes wrong. The investment is absolutely worth it though. My stress levels during tax season dropped dramatically once I could instantly find any document I needed instead of digging through folders. Good luck with your decision!

Could it be that you have a Roth 401k instead of a traditional one? Roth 401k contributions are still reported in Box 12 but with code AA instead of D. Might be worth checking what type of 401k you have.

I had a similar issue last year where my Box 12 was completely blank despite making 401k contributions all year. In my case, it turned out that our payroll system had a glitch that affected about 20 employees out of 200+ at my company. What helped me was gathering all my paystubs from the entire year and creating a simple spreadsheet showing the 401k deductions from each pay period. When I presented this to HR along with my account statement from our 401k provider (showing the actual deposits), they were able to quickly identify the error and issue a corrected W-2c within about 10 days. One thing to check - log into your actual 401k account and verify that all your contributions actually made it into the account. In rare cases, there can be issues where money is deducted but not properly transferred to the retirement plan provider. If the money is there, it's just a reporting error. If it's not, that's a much bigger problem that needs immediate attention.

I'm actually an inventory specialist for an e-commerce company, and we deal with this kind of thing all the time. One thing nobody mentioned - you should also check if your accounting software has an "inventory adjustment" feature that can help document this change properly in your books.

One thing I'd add that hasn't been mentioned yet - make sure you implement better inventory tracking procedures going forward to prevent this from happening again. I learned this the hard way after dealing with a similar issue. Consider doing quarterly mini-counts of your high-value or fast-moving items instead of waiting for year-end. Also, if you're using spreadsheets to track inventory, consider upgrading to proper inventory management software that integrates with your accounting system. The peace of mind from accurate counts is worth the investment. The IRS tends to be more understanding when they can see you've taken steps to improve your processes after discovering an error. Document any new procedures you put in place - it shows good faith effort and professional growth as a business owner.

Has anyone looked at what your CPA's engagement letter says? Mine has language about "utilizing staff and third parties" for tax preparation. I never noticed it until I actually read the fine print last year. Might be worth checking if you agreed to this already without realizing it.

This is definitely something worth questioning, and you're not wrong to feel put off by it. I went through something similar last year with my long-time CPA firm. What helped me make the decision was asking for specifics about their outsourcing arrangement. I requested a meeting to discuss exactly what parts of my return would be outsourced, what security protocols they had in place, and how their review process worked. Turns out they were outsourcing to a firm in India that specialized in US tax prep, but my CPA only spent about 15 minutes reviewing the completed return before filing. For a $450 fee and a relatively straightforward return like yours, I'd expect more personal attention. I ended up switching to a smaller local CPA who handles everything in-house. The price was actually $50 less, and I have direct contact with the person preparing my taxes. My advice: ask your current CPA for a detailed breakdown of their outsourcing process and consider getting quotes from other local preparers. You might find better service for the same price or less.

Did you receive a W-2G form from the casino? Usually they only issue those for certain winning thresholds ($1,200+ for slots, $5,000+ for poker tournaments, etc). If you got a W-2G, the IRS is already expecting to see that income on your return.

This is a really tough situation that catches a lot of people off guard! The tax code around gambling can be pretty harsh. Just to add to what others have said - make sure you're also aware of the gambling loss deduction limits. You can only deduct gambling losses up to the amount of your gambling winnings for the year, and only if you itemize. Since you broke exactly even, you're in the right ballpark there. But as others mentioned, if your total itemized deductions (gambling losses + mortgage interest + charitable donations + state/local taxes + medical expenses over 7.5% of AGI) don't exceed your standard deduction, you're better off taking the standard deduction even though it means paying tax on those winnings. It might be worth running the numbers both ways - itemized vs standard - to see which gives you the better overall result. Sometimes even paying a little extra tax is worth it if the standard deduction saves you more money overall.