Thanks for this clarification! The deadline thing was confusing me. I do have their W-9s collected already, so that part is covered at least. Do you know if there's any benefit to filing electronically versus paper, assuming I can get either done by the right deadline?

Filing electronically has several advantages over paper filing. First, you get that extra month (until March 31) to file with the IRS. Second, electronic filing significantly reduces the chance of errors since validation checks happen automatically. Third, you get immediate confirmation that your forms were received, unlike paper filing where you have no proof of receipt. Also, if you have to file 1099s for more than 10 contractors, you're required to file electronically anyway. Even with fewer forms, electronic filing is generally faster, more secure, and gives you better records for your business.

Is this true for the cheaper versions of QuickBooks too? I have QB Self-Employed and wasn't sure if that includes 1099 filing or if it's only in the more expensive tiers.

Thanks for the insider perspective! If I do decide to just prep this year's return, can I still benefit from their expertise without paying for the full package? I'm worried that if I don't get the multi-year review, I might miss something important from previous years.

You absolutely can benefit from their expertise on just this year's return. A good tax professional will naturally flag any concerning items they notice while preparing your current return, even without doing a formal review of previous years. If they spot something that looks like it might have been an issue in prior years, they'll mention it to you. Then you can decide whether it's worth paying for a more thorough review of those specific past returns. This more targeted approach often saves money while still addressing the most important issues.

I used H&R Block's premium service for a similar situation (RSUs and multiple states) and it was a disaster. They missed several deductions and didn't properly account for the double taxation issues between states. Had to file an amended return with a real CPA later. Would not recommend for truly complex situations.

What's considered "lavish"? Is there like a specific dollar amount per person that triggers IRS attention? I sometimes serve nice scotch to clients because it's relevant to my business discussions.

There's no specific dollar amount defined by the IRS for what's considered "lavish" - it's somewhat subjective and depends on your business context. If serving premium scotch is ordinary and necessary in your industry (like if you work with high-net-worth clients or in an industry where this is standard practice), you can make a reasonable case for it. The key is whether the expense is appropriate for your business context. A $200 bottle of scotch might be perfectly reasonable for financial advisors meeting with wealthy clients, but could be questioned for a web design business meeting with small business owners. Document why the expense is appropriate for your specific business situation and client relationships.

Do you think it's better to just avoid serving alcohol altogether? I'm worried about the extra scrutiny.

Thanks for the TurboTax suggestion. The $200 price tag is definitely more reasonable than $850! Is there a significant learning curve the first time you use it for trust returns? I'm trying to gauge how much time I should set aside to figure this out.

The first year took me about 3 hours to get everything set up and understand how the trust taxation works. The software walks you through everything step by step, but there are some trust-specific concepts that take a bit to wrap your head around. The second and third years were much faster - maybe 45 minutes total since all the trust's basic information was already saved in the system. If your trust has straightforward income like interest or dividends, it's pretty manageable. The only tricky parts tend to be understanding when income is taxed at the trust level versus passed through to beneficiaries.

VITA programs typically only handle basic 1040s with income under certain limits. I've never seen one that handles fiduciary returns like 1041s for trusts. Are you sure about this info?

I found the opposite - the tool kept giving me different answers based on how I entered basically the same information. Ended up just using TurboTax which made it much clearer.

Try using Microsoft Edge or Safari instead. I had the same issue and switching browsers fixed it. Also make sure you're not using any adblockers or privacy extensions when on the IRS site - those sometimes interfere with their tools.