Has anyone tried H&R Block's self-employed software? My situation is similar to the original poster - about $80k income, minimal expenses. Not sure if it's worth the higher price compared to TaxAct or TurboTax Self-Employed.

I made the switch from an accountant to DIY last year and it was honestly easier than I expected! For someone at your income level with straightforward expenses, you're probably right about saving money. I ended up going with TurboTax Self-Employed because it integrates well with QuickBooks if you decide to use that for tracking during the year. The software does a good job walking you through Schedule C and catches a lot of deductions I might have missed - things like business use of home, professional subscriptions, even some travel expenses I hadn't thought about. One tip: start tracking everything now rather than trying to reconstruct it all at tax time. Even if you just use a simple spreadsheet or app to categorize expenses as you go, it'll save you hours come April. The mileage deduction alone can add up to significant savings if you drive for work at all. The peace of mind was worth way more than the software cost, and I actually learned a lot about my business finances in the process!

17 Has anyone else noticed that HSA providers sometimes have different rules about documentation for reimbursements? My provider requires itemized receipts while my friend's just needs basic proof of payment. It's super confusing!

Unfortunately, since your medical expense occurred in September but you didn't establish your HSA until October 1st, you cannot reimburse yourself for that $4,100 expense. The IRS is strict about this - qualified medical expenses must be incurred after your HSA establishment date to be eligible for tax-free reimbursement. However, you can still maximize your HSA benefits going forward! You should definitely contribute up to the annual limit ($4,300 for 2024 individual coverage) to get the tax deduction. Then use your HSA funds for any future medical expenses - there's no time limit on when you need to spend the money, and it grows tax-free. Keep that $4,100 receipt though - if you have any medical expenses from October 1st onward this year, you can reimburse yourself for those once you build up your HSA balance. The key is the service date, not the payment date.

When did you file? I filed 2/12 with TurboTax and my transcripts just updated today with DDD of 3/17 too. Seems like a bunch of us are in the same batch of refunds.

I have an Emerald Card and got the same DDD of 3/17! Filed on 2/8 and was accepted same day. This is my second year with the card and last year they deposited exactly on the DDD date - it showed up around 2 AM that morning. I wouldn't count on it being early, but at least H&R Block is reliable about getting it to you on the actual date. The waiting is torture though, especially with a bigger refund like yours! I keep refreshing the app even though I know it won't change until the 17th 😅

One more thing - make sure u get everything in WRITING from both companies! I had a similar issue and my 1st company promised verbally they would "handle the tax stuff" when I repaid my relo $$ but then when tax time came they were like "not our problem" and I had no proof of what they promised. ended up with a huge headache trying to fix it. get EVERYTHING in email at minimum!!

Another option to consider is consulting with a CPA who specializes in employment tax issues, especially since you're dealing with two states (Oregon and Colorado) which might have different state tax implications for relocation payments and repayments. Some states treat relocation reimbursements differently than federal taxes do, and since you'll be working in Oregon temporarily then moving to Colorado, you might have state tax filing requirements in both states. A CPA can help you understand if there are any state-specific rules about how to handle the repayment, especially if the timing crosses state residency changes. Also, keep detailed records of ALL your actual relocation expenses (receipts for movers, travel, temporary lodging, etc.) because even though you're repaying the Oregon money, you might be able to deduct some actual expenses on your federal return depending on your situation. The Colorado relocation money will also need to be handled properly for tax purposes. This is definitely complex enough that professional help could save you money and headaches in the long run!

Has anyone figured out how to handle the foreign tax paid section on the Stash 1099-B? Mine shows I paid like $4.32 in foreign taxes on some international ETF and idk where to put that in TurboTax?

I went through this exact same nightmare with my Stash 1099-B last year! Here's what finally worked for me: In TurboTax, go to Federal → Wages & Income → Investment Income → Stocks, Mutual Funds, Bonds, Other. Then select "Start" next to "Sales of stocks, mutual funds, etc." The key thing that saved me was realizing that Stash often breaks down your transactions differently than other brokers. Look for the "Summary" section on your 1099-B first - this will show your total short-term and long-term gains/losses. You can often enter these as summary amounts rather than going transaction by transaction. For the cost basis question that's confusing you - if your form shows "Various" in the date acquired column or has a "V" code, select "No, it was not reported to the IRS" and you'll need to enter your purchase info manually. If it has specific dates and amounts, select "Yes, it was reported." Don't stress too much about perfection - as long as you report all the income shown on the 1099-B, you're in compliance. The IRS already has a copy of your form anyway.