I'm open to alternatives for sure! Did TaxAct handle all the rental property stuff well? Like depreciation and splitting expenses between properties? I've just been using TurboTax for so long I'm kinda afraid to switch and miss deductions.

TaxAct definitely handled all the rental property features well. The depreciation calculator is actually more detailed than TurboTax's in my opinion, and I was able to track expenses separately for each property without any issues. You won't miss deductions - if anything, I found TaxAct was more thorough in asking about potential deductions specific to rental properties. The interview process asks about things like travel to inspect properties, home office use for property management, and even partial business use of vehicles for property maintenance. The learning curve isn't bad at all if you're already familiar with tax concepts.

Also check your employee benefits portal if you work for a medium-large company! My employer offers a corporate discount code for TurboTax that saved me like $40 last year, and I had no idea until I randomly checked our benefits site.

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).

Do you just manually calculate your portion each month, or have you found a way to automate this? My bill varies slightly each month so I'm always having to recalculate.

I manually calculate it each month since my bill does vary slightly. I keep a simple spreadsheet that shows the total bill, my portion, and the 50% business use calculation. This takes me about 2 minutes each month but provides a clear audit trail. I know some people set up a fixed monthly amount based on an average, but I prefer the exact calculation each month for accuracy.

I use Zoho Analytics and it's great for this. I created a custom dashboard that pulls my expense data and shows trends in my split costs. You can set up categories for "fully business" vs "partially business" expenses and track them separately.

That's exactly what I needed to know! I'll look into setting up that dashboard. Do you track the percentages separately or just the dollar amounts?

Really? That's interesting. My HR department said the 3921 form was all I needed and that I'm responsible for figuring out the taxes. I'll double check with them about the W-2 reporting. If they won't issue a corrected W-2, is there any downside to reporting it as "Other Income" instead?

There's not really a downside to reporting it as "Other Income" - you'll pay the same amount of tax either way. The main difference is that Other Income isn't subject to FICA taxes (Social Security and Medicare), whereas if it were on your W-2, it would be. Many companies don't correctly report ISO disqualifying dispositions on W-2s because their payroll systems aren't set up to track when employees sell shares. That's why they issue the 3921 form but leave the tax reporting to you. Just make sure you have documentation of everything in case you're ever audited. The 3921 plus your brokerage statements showing the sale should be sufficient.

If you haven't exercised yet, you have options to possibly reduce taxes. The key is to try to get a qualifying disposition rather than disqualifying. To do this, you need to: 1) Hold the shares for at least 1 year after exercise AND 2) Hold the shares for at least 2 years after the option grant date If you meet both conditions, only the difference between sale price and strike price is taxed, and it's taxed as long-term capital gains (usually lower rates) rather than ordinary income.

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.