Would it be better to file as a Schedule C business loss or just take the casualty loss directly? Does it make a difference tax-wise? I'm in a sorta similar situation with my small side business.

You'll definitely want to file Schedule C to report all your business income and expenses, including the equipment that was destroyed. The casualty loss is reported on Form 4684, but since these were business assets, the loss ultimately flows to your Schedule C. Filing the business loss on Schedule C is generally more advantageous than taking a personal casualty loss because personal casualty losses are highly restricted under current tax law (only federally declared disasters qualify). Business casualty losses don't have these same limitations and can offset your other income.

The key difference between a hobby and a business isn't whether you made money yet, but whether you had a reasonable expectation of making a profit and were operating it in a businesslike manner. Plenty of legitimate businesses have losses in their first year or even several years.

Thank you so much for this suggestion! I didn't know the SSA would have that information. Do they show the tax withholding amounts too or just the total income? And how quickly does that information get updated?

The SSA only shows your total earnings, not the withholding amounts. So it will help confirm your income, but you'll still need to estimate your federal and state tax withholding from the pay stubs you have. It typically gets updated a few months after the end of each quarter, so there might be some lag. But it's a good way to verify your total earnings when you don't have complete records. Even partial confirmation is better than nothing when you're filing a substitute W-2 form.

This is definitely an option, but there can be a significant delay. W-2s aren't required to be filed with the IRS until January 31st, and then it takes time for them to be processed and appear in your transcript. If the company closed and never filed them at all (which sounds possible in OP's case), they won't show up at all.

Thanks for mentioning the treaty! I'll look into that. Regarding the FEIE, my accountant originally suggested using Foreign Tax Credits instead because the Dutch tax rates are higher than US rates, so I'd potentially get more benefit from the credits. Does that sound right, or should I reconsider using the FEIE?

Your accountant's reasoning about FTC vs FEIE is generally sound. When foreign tax rates are higher than US rates, the Foreign Tax Credit usually provides better results since it directly offsets your US tax liability dollar-for-dollar and can generate excess credits to carry forward. However, there's a potential hybrid approach worth considering: use the FEIE for your employment income and then use FTC for your investment income. This sometimes creates a more favorable tax situation, especially when dealing with the basketing limitations. The key advantage is that by excluding your earned income entirely from US taxation with the FEIE, the remaining investment income might fall into lower tax brackets, potentially reducing your overall US tax liability.

Yes, I completed streamlined last year with this exact issue. The key is to be consistent across all three tax years you're filing. Make sure your approach to categorizing income in the different baskets follows the same methodology for each year. In my certification statement (Form 14653), I specifically mentioned that I was uncertain about certain aspects of Form 1116 basketing but had made good faith efforts to comply based on my understanding of the rules. The IRS accepted my submission without any questions.

Thank you for the specific steps! This makes a lot of sense. I checked my tax software again and I think I discovered the issue - there's a specific question about "Do you qualify to deduct your IRA contributions?" that I must have answered incorrectly. Previous years I knew to say "No" but this year with the job change and severance, I might have clicked "Yes" by mistake. I'll try redoing those steps in the correct order. Would it also make sense to just delete all my IRA entries and start fresh with these steps in mind?

Yes, I'd recommend deleting all the IRA-related entries and starting fresh. That's the cleanest approach. Some tax software doesn't handle corrections well when it comes to the 8606 form. When you restart, just follow those steps in order. The key is definitely that "Do you qualify to deduct" question - that's the exact one that determines how the software handles everything downstream. Always answer "No" for a backdoor Roth strategy since the whole point is you're over the income limits for deductible contributions. And don't worry about the severance - it's just regular income. It doesn't change how backdoor Roth contributions work. The W-2 Box 13 check is typically for retirement plan participation at that employer, which is separate from your individual IRA strategy.

I haven't heard about increased scrutiny, but I can tell you that reporting Backdoor Roth incorrectly is definitely a red flag. When your 1099-R shows a distribution (the conversion) but there's no corresponding basis tracking on Form 8606, it creates a mismatch that their systems can easily detect.

This is so helpful! Quick question - what if the pay schedules are different? I teach at one college that pays monthly and another that pays biweekly in the same system. Does that mess up the withholding calculations?

Different pay schedules shouldn't mess up your annual withholding in the end, but it can cause some variation in how much is taken from each paycheck. The withholding system is designed to estimate your annual tax based on the frequency of your pay periods. When you have different schedules, each payroll system is making its own calculation based on that specific payment. The good news is that it all reconciles at the end of the year on your W2. If you want your withholding to be more consistent, you can use the "extra withholding" line on your W4 to specify an additional amount to withhold from one of your paychecks to make up any difference.

Yes, you absolutely should be checking the multiple employers box! Since you're getting two separate W2s from different university systems, those are definitely separate employers with different EINs (Employer Identification Numbers).