Just a heads up - don't forget about self-employment taxes! Even if you write off the excavator, you'll still owe SE tax (15.3%) on your net profit. A lot of people start side businesses and get shocked by this at tax time.

One thing I'd add to all the great advice here - make sure you're prepared to demonstrate the business nature of your activity if the IRS ever questions it. Since you bought the excavator in November but won't start generating income until spring, document everything that shows your serious business intent: research you did on pricing for excavation services in your area, any business cards or flyers you've made, social media pages you created, networking with potential clients, etc. Also consider getting business insurance for the excavator once you start operating. Not only is it smart protection, but the premiums are another business deduction. And if you're planning to operate it on other people's property, many clients will require you to have liability coverage anyway. The fact that you're asking these questions and thinking ahead shows you're taking this seriously as a business venture, which is exactly the kind of profit motive the IRS looks for. Good luck with your new excavation business!

Has anyone dealt with this situation using TaxSlayer? I'm having the exact same Roth IRA withdrawal issue but I can't find where to enter my contribution information to offset the 1099-R. The software keeps treating my entire withdrawal as taxable.

I went through this exact situation last year and it's definitely stressful! The good news is that you're absolutely right - Roth IRA withdrawals of contributions should be tax-free. The key issue is that your tax software doesn't automatically know how much of your withdrawal was contributions versus earnings. Here's what worked for me: First, make sure you have Form 8606 Part III completed correctly. You'll need to track down your total Roth contributions from all years - this becomes your "basis." Since you contributed $15,000 total and withdrew $13,200, your entire withdrawal should be considered a return of contributions and therefore not taxable. In FreeTaxHelper, look for a section on "Retirement Account Distributions" or specifically "Form 8606." You might need to manually override what the software is calculating based on just the 1099-R. Don't panic about that $3,800 tax bill - once you properly account for your contribution basis, it should drop significantly or disappear entirely. Keep good records of all your contributions going forward, as you'll need this information for any future withdrawals. The 5498 forms are indeed just informational, but they're invaluable for tracking your basis over time.

5 Has anyone tried applying for an ITIN through a Certified Acceptance Agent (CAA) instead of mailing documents directly to the IRS? I've heard this might be faster and you don't have to send your original documents to the IRS. I'm in the same situation as OP and trying to figure out the best approach.

16 Just wanted to add something important that nobody mentioned yet - be careful with amending your return from single to married filing jointly after getting the ITIN. If your spouse is a nonresident alien, they generally can't file jointly with you UNLESS you make a special election to treat them as a resident alien for tax purposes. This election has pros and cons - it might lower your tax bill, but it means your spouse's WORLDWIDE income becomes taxable in the US. So if they have income in their home country, you'd need to report that too. Form 8840 is used for this election. Just something to consider before you rush to amend!

Has anyone had success deducting their health insurance premiums as a medical courier? I'm spending almost $900/month and I've heard conflicting advice about whether it's fully deductible or not.

As someone who's been doing courier work for a few years, I can't stress enough how important it is to keep meticulous records from day one. That 145K miles annually is going to be your biggest deduction - potentially worth over $99K at the current rate. A few additional tips that helped me: 1. Open a dedicated business checking account immediately. Keep ALL business expenses separate from personal. This makes bookkeeping so much easier and looks more professional if you ever get audited. 2. Consider getting a business credit card for gas and maintenance. Many offer cash back on gas purchases, plus it automatically separates your business expenses. 3. Don't forget about smaller deductions that add up: phone bill (business portion), GPS/navigation apps, work uniforms/safety gear, and even things like hand sanitizer or masks if required for medical deliveries. 4. With that income level, you'll definitely want to max out retirement contributions. A SEP-IRA lets you contribute up to 25% of your net self-employment income, which could significantly reduce your tax burden. 5. Keep receipts for EVERYTHING vehicle-related even if you use standard mileage. If your car gets totaled or needs major repairs, you might want to switch methods mid-year. The key is staying organized from the start. It's much harder to reconstruct records later, especially with the IRS scrutinizing high-mileage claims more closely these days.

Be extremely cautious about this situation. In 2023, my check showed as mailed on April 12th, but wasn't actually sent until April 28th - exactly 16 days later. When it didn't arrive by April 26th, I filed Form 3911 thinking it was lost. This created a complete mess in their system because they had to cancel the check that hadn't actually been sent yet, then reissue a new one. The entire process took 9 weeks and 4 days to resolve, and required 3 separate calls to the IRS. Always wait at least 4 weeks from the WMR mail date before taking any action.

This is incredibly helpful information! I'm currently in week 3 of waiting for a check that WMR says was mailed March 1st. Based on what everyone is sharing here, it sounds like I should call to verify the actual mail date before panicking. The fact that the IRS has multiple systems that don't sync properly explains so much frustration I've had in past years. Does anyone know if there's a specific number or department that's best for checking actual mail dates, or is it just the general refund hotline? I want to make sure I'm calling the right place to get accurate information.