One thing I haven't seen mentioned here is quarterly estimated tax payments. If you're making significant profits on Kalshi (like the original poster's $8,400), you might need to make quarterly estimated payments to avoid underpayment penalties. Since prediction market earnings are treated as "other income" and taxed at ordinary rates, they're not subject to withholding like W-2 wages. The IRS expects you to pay as you go throughout the year, not just when you file your return. If your Kalshi profits plus other income mean you'll owe more than $1,000 in taxes for the year, you should probably be making quarterly payments. This caught me off guard my first profitable year - I owed a $180 underpayment penalty even though I paid my full tax bill on time. The safe harbor rule is to pay at least 100% of last year's tax liability (110% if your prior year AGI was over $150k) through withholding and estimated payments combined. Worth calculating this if you're having a good year on prediction markets!

For those asking about quarterly estimated tax tools - I've been using the IRS Form 1040ES worksheet but modified it for prediction market income volatility. What I do is calculate my estimated annual tax liability based on my regular income, then add 25-30% buffer for potential Kalshi profits. The key insight I learned is that you can adjust your quarterly payments throughout the year as your prediction market performance becomes clearer. If you overpaid in Q1-Q2 because you estimated too high, you can reduce Q3-Q4 payments accordingly. The IRS just cares that your total payments meet the safe harbor threshold by year end. One practical tip: I track my running net Kalshi profits monthly and recalculate my quarterly payment needs. This way I'm never surprised by a huge underpayment penalty. The annualized income installment method (Form 2210 AI) can also help if your income is really uneven throughout the year - it lets you match your quarterly payments to when you actually earned the income. The 110% safe harbor rule has saved me from penalties even in years when my prediction market income was all over the place.

Back in 2022, I had an unemployment overpayment of $4,200 that was going to be offset from my taxes. I found out that Texas has specific exemptions for people experiencing homelessness with dependents. I had to provide a letter from the shelter I was staying at and copies of my children's documentation. They reduced my overpayment by 80% and set up a $25/month payment plan for the rest. The key was getting it all submitted before the Treasury Offset Program certification date, which happens in early February for most states.

I went through this exact same nightmare when I was homeless with my two kids in Houston. Here's what saved me: Call TWC at 800-939-6631 early morning (7 AM sharp) and ask for the "Collections Department" specifically. Don't get transferred around - insist on collections. Tell them you need an "Emergency Hardship Waiver" due to homelessness with minor children. They have a form called TWC-175 that most people don't know about. I got mine processed in 8 days and they waived 100% of my $3,100 overpayment. Also, if you're staying at a shelter, get a letter on letterhead from them TODAY - this carries more weight than you'd think. The woman who helped me said homeless families with kids get priority review. Don't give up, the system actually does work if you know exactly what to ask for.

called them yesterday and the lady said there experiencing delays due to high volume rn. might take up to 14 business days smh

Been waiting on my Kansas refund for 12 days now and starting to get worried. Filed electronically on Jan 28th, got accepted same day, but still nothing in my account. Called their hotline twice and just got the generic "processing takes 7-14 business days" message. Really hoping it shows up soon since I need it for some bills. Anyone else experiencing longer delays this year?

Just a heads up, I was having the same issues with TaxAct but found that it works if you use Microsoft Edge in InPrivate mode. Something about their scripts conflicts with certain browser extensions. Not ideal but might help if you're stuck with them and can't get a refund.

This is why I never pay for tax software until I'm ready to file. I always use the free version to input everything, then only upgrade at the very end if I need to. That way if there are issues, I haven't spent any money yet. TaxAct worked fine for me last year but I'm avoiding them this year after seeing so many complaints.

Have you considered using a tax professional instead of DIY software? I used to struggle with Schedule E every year until I found a CPA who specializes in real estate. She charges $350 but saved me over $2000 in deductions I was missing.

I feel your pain with FreeTaxUSA's Schedule E limitations! I ran into similar issues last year with depreciation calculations that just wouldn't compute correctly. One thing that helped me was double-checking that I had entered my property's placed-in-service date correctly - sometimes even a small error there can throw off the entire depreciation calculation. For this year, I ended up using TaxSlayer Premium which handles Schedule E much better than FreeTaxUSA. It's about $60 but allows manual overrides on depreciation calculations when their automatic calculations don't work. The interface isn't as clean as some others, but it gets the job done for rental properties. If you're comfortable with your Excel template and it's been working for 8 years, honestly you might want to stick with what works. You could prepare your Schedule E in Excel and then manually enter those final numbers into whatever e-filing software you choose, just to get the electronic filing benefit.