Oh no, I didn't even think about this! So I need to make sure the 1099s are actually filed with the IRS too? My new preparer didn't mention anything about that specifically, just that we were amending my returns. Now I'm worried again...

Yes, you absolutely need to make sure the 1099-NECs are filed with the IRS! There are two parts to this process: sending copies to your contractors (which they need for their own tax filing) AND submitting them to the IRS. The deadline for filing 1099-NECs with the IRS is January 31st of the year following payment, so your 2022 forms were technically due January 31, 2023. There are penalties for late filing, but they're relatively small for small businesses if you file within 30 days of the deadline. The penalties increase the longer you wait, but filing late is still much better than not filing at all.

The penalties can actually be much higher depending on how many contractors and how late the filing is. I got hit with a $250 per contractor penalty for missing 1099s for my wedding video business. Definitely ask your preparer about this!

Wait, are you saying if I was owed a refund for 2013, I can't get it anymore? But if I owe THEM money, I still have to pay? That doesn't seem fair at all. How do I even know which situation I'm in before I file?

Yes, unfortunately that's exactly how it works. The IRS gives you 3 years to claim refunds, and after that window closes, you generally can't get that money. But they can still collect from you virtually forever (there's a 10-year statute of limitations on collection, but with many exceptions that can extend it). You won't know for certain which situation you're in until you prepare the return. That's why it might be worth working through the forms or using a service to calculate it first, before officially filing. If it turns out you owe a substantial amount with penalties, you might want to consult with a tax professional about your options.

I used FreeTaxUSA for a 2014 return last year and it worked well. It was around $15 for the federal (they keep all the old tax year versions available) and another $15 for state if I remember right. Much cheaper than TurboTax. The interface isn't as fancy but it gets the job done and had all the forms I needed.

Does that mean I'm in trouble if I sometimes move some of my inventory boxes around when I need to vacuum or clean? The space is definitely dedicated to my business but occasionally I need to shift things for maintenance.

No, you're not in trouble for basic maintenance activities like cleaning. That's considered a normal part of maintaining your business space. What the IRS looks for is whether the space serves a dual purpose. For example, if you're storing inventory in your bedroom where you also sleep, or using your living room couch for both business and personal activities, those spaces wouldn't qualify. But if you have boxes of inventory in a dedicated area and just move them temporarily to clean, that's perfectly fine.

I used TurboTax last year and it walks you through both methods and shows you which one gives you the bigger deduction. It asks for your total home square footage, the business-use square footage, and your expenses. Pretty straightforward. But honestly, I still got confused with some of the questions about "exclusive use" and partial room usage. Had to google a bunch of stuff that wasn't clear in the software.

I actually used a big chunk of my AMT credit two years after I got hit with a massive AMT bill from ISOs. The key was that my income dropped significantly that year (took some unpaid leave), which lowered my regular tax enough that it was less than what my AMT would have been without the credit. The credit essentially brings your AMT down to your regular tax amount. So you need a year where your regular tax would naturally be lower than your AMT for the credit to kick in.

Wait the IRS actually pays interest when they're late with your refund? Is that automatic or do you have to request it somehow?

It's completely automatic! The IRS pays interest on refunds that are issued more than 45 days after the filing deadline (or the date you filed, if you filed after the deadline). The interest is calculated from the original due date of the return. The interest rate changes quarterly based on federal rates. Currently it's around 7% annually which is pretty decent. The interest gets added to your refund automatically - you'll see it as a separate amount on your refund check or direct deposit description. You will get a Form 1099-INT the following January because that interest is taxable income for the year you receive it.

States all have their own rules unfortunately. What state are you in? I know NY and CA don't penalize for late filing if you're due a refund, similar to federal.