Wait, that's super relevant to us! My husband has about $45,000 in student loans on an income-based plan. How would filing separately affect his payments? Would the tax hit be worth the loan payment savings?

The impact depends on the specific repayment plan he's enrolled in. If he's on an Income-Based Repayment (IBR), Pay As You Earn (PAYE), or Income-Contingent Repayment (ICR) plan, filing separately could potentially lower his monthly payments significantly because they'll only count his income rather than your combined household income. Whether it's worth it requires calculating both the tax difference and the loan payment savings. For example, if filing separately costs you $1,000 more in taxes but saves $150 monthly on loan payments ($1,800 yearly), you'd come out $800 ahead. Many people in your situation find that the student loan savings outweigh the tax inefficiencies, especially if the income disparity between spouses is significant.

You're right about the standard deduction but wrong about married filing separately. MFS doesn't get the single filer standard deduction - both spouses have to take the same type of deduction (either both itemize or both take standard). And if one itemizes, the other MUST itemize even if they have zero deductions. This trips up a lot of people.

Yes, as a 1099 contractor you can absolutely deduct mileage for driving between job sites (but not commuting from home to your first job site of the day or from your last job site back home). For 2025, you can either take the standard mileage rate or track actual expenses like gas, maintenance, etc. The standard rate is usually easier - just keep a log of business miles driven. Also keep those receipts for tools and work clothes! Those are legitimate business expenses you can deduct on Schedule C.

Make sure your boss is actually classifying you correctly! Some employers try to call people "contractors" to avoid paying employment taxes when legally they should be treating them as employees. If they control WHEN and HOW you do the work (vs just the end result), you might actually be misclassified.

Are you a W-2 employee? If yes, then unfortunately no - those home expenses aren't deductible for regular employees anymore. If you're a 1099 contractor, then yes you could deduct the business portion of those expenses (would need to calculate what % is for work vs personal use).

Oh that's interesting! I hadn't considered that. I worked for a startup so it's totally possible they messed something up with the reporting. How did you end up resolving your situation? Did you have to get documentation from your employer?

I had to get a corrected Form W-2 from my employer showing the stock compensation was included in my wages. Then I had to write a detailed letter to the IRS explaining exactly how the income was reported on my tax return (which line number, which form, etc.) and included copies of my brokerage statements showing the transactions. The key was getting someone from our HR/payroll department to provide a letter confirming how they had reported it to the IRS. Once I had that documentation and sent everything certified mail, it eventually got resolved. Just be prepared for it to take several months.

Tax advocates are nearly impossible to get right now unless you're facing "significant hardship" like eviction or utilities being cut off. They're seriously understaffed and have strict criteria for who they'll help. I tried for months and kept getting rejected.

Is there any way to tell if I actually owe money to the state vs federal? I'm paranoid I'm going to mail something to the wrong place and then get in trouble for not paying.

Would an email work instead of certified mail? I have all their texts demanding payment for the shirts, but I'm not sure I want to spend money on certified mail to these jerks.

Email isn't ideal because it's easier for them to claim they never received it. The certified mail creates an official record that they received your communication, which is important if this escalates further. The $4-5 for certified mail is worth it for the paper trail it creates. That said, if you do use email, make sure to request a read receipt and save all correspondence. The texts demanding payment are good evidence already, so keep those too. The key is documenting everything in case you need to prove harassment later or defend yourself if they try to send this to collections.

That's a good point - OP should look up the IRS Whistleblower Program. If the employer is systematically underreporting wages, the IRS takes that very seriously and you could potentially get a reward if your information leads to the recovery of unpaid taxes. The reward can be 15-30% of what the IRS collects!