Thanks for the direct links! Have you personally used the SSA's BSO system for late W-2 filings? Was it easy to navigate for someone who isn't super tech-savvy?

Yes, I've used the SSA's BSO system for late W-2 filings twice now. It's definitely designed with the average business owner in mind, not just for tech experts. The interface walks you through each step and clearly labels what information needs to go where. For late filings, there's a specific section where you'll see the original deadline and the system acknowledges you're filing late. It doesn't prevent you from proceeding. Just make sure you have all your business information and employee details ready before you start. You can save your progress and come back if needed, but having everything prepared makes it a much smoother process.

This is super important! I completely forgot about state W-2 filing and got hit with a $200 penalty from my state last year even though I filed the federal one.

Thanks for sharing these details! Are there any specific payroll services you'd recommend for a one-person S-Corp? And did you find any advantages besides the SE tax savings?

I use Gusto for payroll and it's pretty straightforward for a one-person operation. The interface is simple and they handle all the tax filings automatically. Some others use Square Payroll or OnPay, which are a bit cheaper. Beyond the SE tax savings, I've found some additional benefits. Having a business entity has helped me land bigger clients who prefer working with corporations over individuals. I can also now contribute to a Solo 401k as both employer and employee, which has increased my retirement savings options. The structure has also forced me to be more disciplined with my business finances and separate them properly from personal expenses.

Can you explain this a bit more? I thought QBI applied the same whether you're sole prop or S-Corp?

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.

Is there an easy way to track all this stuff for next year? I'm just starting some side gig work and tax season already seems daunting.

Oh no, I had no idea about the extra tax! Do you think I'll owe a lot on $3,400 of contractor income? I'm already getting a small refund from my W-2 job so I was hoping that would cover any extra taxes.

on $3,400 you're looking at around $480 just for self-employment tax (social security and medicare) before regular income tax. your refund might cover it, but it's definitely eating into what you would have gotten back. for next year, a good rule of thumb is to set aside about 25-30% of any contractor income for taxes. and yeah once you hit around $1000 in expected tax liability from self-employment, you're supposed to make quarterly payments to avoid underpayment penalties. it's a pain but better than a surprise bill!

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?