Do you know if converting from an FSA to HSA mid-year affects the contribution limits? My company is switching our health plans in July and I already contributed to an FSA.

Yes, it definitely affects your contribution limits. When you switch from an FSA to HSA mid-year, you generally have to prorate the HSA contribution limit based on the number of months you're eligible. If you make a mid-year switch, you can only contribute 1/12 of the annual limit for each month you're HSA-eligible. However, there's something called the "last-month rule" that might help - if you're HSA-eligible on December 1, you can potentially contribute the full year's limit, but you must remain HSA-eligible through December of the following year (called the testing period) or face penalties on the accelerated portion.

Does FreeTaxUSA handle situations where you've changed jobs mid-year and have HSA contributions from two different employers? That's what I'm dealing with now.

Do you think it's worth hiring a CPA who specializes in real estate for the first year at least? I'm concerned I'll mess this up, and it seems like getting it right from the start would be easier than fixing it later.

Absolutely worth hiring a real estate specialized CPA at least for the first year. They'll set up your depreciation schedules correctly from the beginning, which makes future years much easier. The upfront cost of a good CPA is nothing compared to the potential headache of incorrectly calculated depreciation that might need to be fixed through amended returns. Plus, a real estate CPA will know about deductions and strategies you might miss on your own. My biggest regret was trying to DIY my rental taxes for the first few years - I missed several legitimate deductions and had to go back and amend returns once I finally got professional help.

Yes, what you're referring to is a cost segregation study, which is essentially a more detailed version of what we're discussing. A professional cost segregation study identifies many building components that can be depreciated over 5, 7, or 15 years instead of 27.5 years. This might include electrical systems, plumbing, specialized flooring, cabinetry, and many other components. The benefit is accelerated depreciation deductions, meaning larger tax savings in the early years. However, a formal cost segregation study typically makes financial sense only for properties valued at $500,000+ because of the cost to have it professionally done. For smaller properties, you can still segregate obvious components (like appliances and land improvements) without a formal study, but you won't be able to get as detailed with building components.

What happens if the numbers don't match between my last pay stub and W-2? My retail job's W-2 shows about $200 less in income than my December pay stub indicated for the year.

If there's a discrepancy between your W-2 and pay stubs, first check if there's a logical explanation. Sometimes the last paycheck of December might be paid in January, which would explain why the W-2 total is lower than your December pay stub shows. If there's no clear explanation, contact your employer's payroll department directly. They can check their records and issue a corrected W-2 (called a W-2c) if needed. Small differences might occur due to non-taxable benefits or other adjustments, but anything significant should definitely be investigated before you file.

Did you have to pay a penalty too or just the interest? I'm worried because I just realized I forgot about a small job I had last year (only made like $600).

10 Do you need to use certified mail? I'm worried about my return getting lost.

8 Yes, absolutely use certified mail with return receipt requested. It costs a bit more at the post office, but you'll get proof of delivery that the IRS received your return. This is crucial if there's ever any question about whether you filed on time. I also recommend making a complete photocopy of everything you're sending before you mail it, including W-2s and other documents. Store these copies somewhere safe in case you need to reference them later or if the IRS claims something was missing.

6 Tax pros have the same October 16th deadline for individual returns. They can efile business returns and some other forms year-round, but Form 1040 (individual returns) are subject to the same cutoff date for everyone.

Do you know if common property rules still apply if you're legally married but have a prenup? Our agreement specifically states our incomes remain separate, but I'm not sure if the IRS cares about that for Form 8958 purposes.

Yes, the IRS does actually recognize prenups for tax purposes in community property states, but the rules are very specific. Your prenup needs to explicitly outline how income and assets should be treated (not just a general "our incomes are separate" statement). You'll still need to fill out Form 8958, but you would allocate income according to your prenup rather than the standard 50/50 split. However, make sure your prenup complies with your state's requirements for it to be valid - some states have very specific rules about prenups overriding community property laws.

Generally, if you bought it before marriage, the original investment stays your separate property. However, any appreciation during marriage is typically considered community property in most community property states. So you'd need to establish the value at the time of marriage and then split the gains from that point forward.