I'm self-employed, running my own consulting business. The conference is directly related to my field and I'm presenting at one of the sessions. Does that strengthen my case for the airfare deduction even with the extended vacation time?

That definitely strengthens your case! The fact that you're presenting at the conference creates an even clearer business purpose for the trip. The IRS would have a hard time arguing that your primary purpose wasn't business when you're actually a presenter. Since you're self-employed, you'll report these deductions on your Schedule C, which is much more straightforward than the old unreimbursed employee expense deductions. Just make sure to maintain documentation of your presentation, the conference agenda showing your name, and all receipts for the business portion. The extended vacation doesn't affect your airfare deduction as long as the primary purpose was clearly business, which in your case is very well established by being a presenter.

I thought the rules were different for meals included as part of a conference registration fee? Aren't those fully deductible rather than subject to the 50% limit?

That's a great idea I hadn't thought of! Have you actually gotten detailed help from them before on how to report specific transactions? I'll definitely give them a call tomorrow if that's the case.

I've gotten basic guidance from them before, but it can be hit or miss depending on who you talk to. Their customer service can usually help clarify what specific codes or entries on your form mean. What they typically won't do is give specific tax advice about how to report things on your return - they'll explain their form but stop short of telling you exactly what to enter on your tax forms. Still worth calling though, as they can often clear up confusion about what certain transactions or adjustments on their statements represent.

I've had mixed results with Reddit. Sometimes you get amazing detailed answers from actual tax pros, and other times you get conflicting advice that leaves you more confused. The challenge is knowing which advice to trust when you get multiple different answers.

That's a really important distinction. How can you tell if your LLC is being taxed as an S-Corp vs a disregarded entity? I filed paperwork when I started my business but honestly don't remember what I selected.

You can tell by looking at what tax forms you've filed in the past. If you've been filing Schedule C with your personal tax return, then your LLC is being treated as a disregarded entity. If you've been filing Form 1120-S and receiving a K-1 from your business, then you elected S-Corp treatment. If you're still unsure, you should be able to check with the IRS. You would have filed Form 2553 to elect S-Corp status. If you never filed that form, then you're most likely a disregarded entity by default. This distinction is crucial for understanding how losses flow through to your personal taxes.

Yes, the rules definitely changed. Starting with tax years after 2020, NOLs can only be carried forward (not back, except for some farming losses). Also, you can only use the NOL to offset up to 80% of your taxable income in any future year. So if you made $10,000 this year, you could only use $8,000 of your NOL, and would have to carry the rest to future years.

Thanks for explaining that! That makes sense why TurboTax was limiting how much I could claim. So I'll have to carry forward part of my loss to next year too. Wish they'd make these tax rules simpler to understand.

Good point about the improvements! For the first house, I actually did replace the roof ($14k) and installed a new HVAC system ($9k). Would I need receipts for all of these improvements or are there other ways to document these if I can't find all the paperwork?

Receipts are definitely the best documentation, but if you don't have them all, there are other options. Bank or credit card statements showing payments to contractors can work. Even emails confirming quotes that you accepted can help establish the costs. For major improvements like a roof or HVAC system, you might also have permit records with your local building department that can verify the work was done. Some contractors might also have records they can provide if you reach out to them. The IRS knows people don't always keep perfect records, but they do expect you to make a reasonable effort to document these costs.

Not necessarily. The test is whether you lived in it as your primary residence for 2 of the 5 years before selling. Who lives in it during other periods doesn't affect that qualification. If OP had rented it out, there might be some depreciation recapture to deal with, but since no rent was collected, that's not an issue.

I just tried to create an account on the IRS site but it's asking for a credit card number or loan account number for verification, which I don't have since I'm pretty young. Is there another way to access this information?

Yes, there are alternative verification methods if you don't have credit cards or loans. You can use information from a previous year's tax return instead. Look for the option that says something like "verify with a tax return" during the identity verification process. If that doesn't work, you can request an in-person appointment at a local IRS office where they can help you set up access. Or as mentioned above, calling the IRS directly (or using a service to help you get through) is another option to get your W-2 information.

I did that last year with my former employer and they got super defensive and rude about it! But they did send my W-2 within 2 days after I mentioned the January 31st requirement lol. Sometimes you gotta be a bit assertive.