Does putting a rental property in an LLC actually save on taxes though? I thought LLCs are pass-through entities so the tax treatment is the same as individual ownership? Also doesn't it make the mortgage situation more complicated?

You're right that a single-member LLC is typically a pass-through entity and doesn't change the tax treatment by itself. I should have been more clear. The tax savings come from strategies you can implement once you have the proper structure in place, not just from having an LLC. The real benefits come when you combine the LLC with proper tax planning like implementing a management company structure or potentially electing S-corp taxation for your activities depending on your situation. And yes, transferring mortgaged properties into an LLC can trigger due-on-sale clauses in some cases, so that's exactly why I recommended consulting with both tax and legal professionals before making any moves.

What app do you use for storing receipts? I've been trying to find a good one that will organize by property and expense type.

This is really helpful, thank you. Do you know if there's a limit on the amount of books/supplies that can count toward the American Opportunity Credit? I spent about $1,800 on books and another $1,200 on my laptop.

The American Opportunity Credit is calculated as 100% of the first $2,000 in qualified expenses, then 25% of the next $2,000 - for a maximum credit of $2,500. Your $3,000 in expenses would qualify for the full first $2,000 plus 25% of the remaining $1,000, so $2,250 total credit. Remember that the expenses must be required for enrollment in your courses, which books typically are. For the laptop, you'll need to determine if it was required for your specific program of study or just convenient. If your courses required specific software or computing capabilities, you've got a stronger case for including it.

This is great advice. My university's VITA program actually helped me file for hardship consideration with the IRS too. They had specific experience with scholarship tax issues since they see it every year with students.

This is super helpful, thank you! Is it worth trying to handle the initial appeal myself to save on costs, or is that risky? I'm worried about saying something that might hurt my case later.

It depends on your comfort level with tax matters and how complex your situation is. For simple factual disputes where you have clear documentation, you might be able to handle the initial response yourself. However, if there are complex legal interpretations at play or if your business structure has nuances, professional help is advised. The biggest risk of handling it yourself is inadvertently making statements that limit your options later or missing technical arguments that could help your case. If you do go it alone for the initial response, be very careful to stick to provable facts and avoid making legal conclusions or interpretations of tax law.

I paid $3,500 for my tax attorney last year for an appeal similar to what OP is describing. It was a flat fee that covered everything unless it went to Tax Court (which it didn't). Some attorneys charge hourly ($350-500/hr where I live) which can add up fast. Ask for a flat fee if possible!

This is solid advice! My employer uses UltiPro and I was able to log in and download my W2 even though I left the company in November. Totally forgot I had that access.

That's great to hear it worked for you! Many people don't realize these payroll portals often maintain your access for a period of time after employment ends, specifically for tax document purposes. If anyone else is trying this method, also check your email for any invitations to these portals when you were hired. Sometimes the login credentials or reset instructions are still valid. Even if your account appears inactive, customer service for these payroll providers can sometimes help former employees access just their tax documents.

Won't an extension delay my refund though? I'm counting on that money for some bills coming up in March.

That's a great point I hadn't thought about. So should I be submitting some kind of expense report to my own S-corp for reimbursement? Or is it enough to just document everything in my company records?

You should definitely be submitting formal expense reports to your S-corp for reimbursement. This creates the proper documentation that shows you're following an "accountable plan" which is critical for this arrangement to work properly with the IRS. The expense report should include the business purpose, dates of travel, locations, and calculation of the per diem amounts based on the State Department rates. Your S-corp should then reimburse you directly for these expenses. In your company records, these would be logged as business travel expenses, and on your personal taxes, the reimbursements wouldn't be considered income since they're under an accountable plan.

I tried using TurboTax for this last year and it was a nightmare. The software doesn't have clear guidance on foreign per diems. I ended up manually calculating everything and entering it as "other business expenses" with detailed notes. Not ideal but it worked.