I use TurboTax Self-Employed and it walks you through business expenses including "uniforms and work clothing." Just make sure you're filing a Schedule C (sole proprietor/independent contractor). I claimed about $750 in specialized performance clothing last year with no issues. Just be accurate and keep your receipts!

Thanks for the info! That's really helpful. I was overthinking it and getting confused about where to put these expenses. Just to clarify, did you have to itemize each clothing piece separately or could you just put a total amount for "performance costumes" or something like that?

That's really helpful! Yes, he did have documented medical issues - he was in and out of treatment programs and had been diagnosed with depression alongside addiction. Would I need medical records or would treatment program documentation be sufficient? And how exactly would I request penalty abatement - is there a specific form?

Treatment program documentation should be sufficient, especially if it covers the tax years in question. Medical records would strengthen your case if you can obtain them, but aren't absolutely necessary if you have good treatment records. For penalty abatement, you'll want to submit Form 843 "Claim for Refund and Request for Abatement" for each applicable tax year. Include a detailed letter explaining how his medical conditions prevented him from meeting his tax obligations. Be specific about timeframes and how his condition impacted his ability to manage financial matters. The IRS calls this "reasonable cause" abatement, and medical issues are one of the stronger grounds for approval.

The fee can be waived entirely if you check the "Low Income Certification" box and qualify. For estates, they look at the gross monthly income of the estate (usually zero) and the assets. With minimal assets as described, the estate likely qualifies for the waiver.

Thanks for this! I didn't even think about the bank interest part. Just checked and I earned about $350 in interest from my savings account last year. Would that show up on some form I should have received?

Yes, your bank should have issued you a Form 1099-INT if you earned $10 or more in interest. Check your online banking portal - most banks now make these forms available electronically rather than mailing them. Look in the statements or tax documents section of your account. If you can't find it there, call your bank's customer service. Even if you didn't receive the form, you still need to report that $350 interest income on your tax return. TaxUSA has a specific section for interest income where you can enter this manually.

Where exactly is this Form Finder in TaxUSA? I've been using it for 3 years and never knew this existed!

Does the holding period start from the day you sign the purchase papers or the day the sale officially closes? My closing took almost 2 months!

The holding period is generally calculated from the day the first sale closes (when you acquired the property) to the day the second sale closes (when you sold it). The date on the closing documents is what matters, not when you signed the purchase agreement. So in your case, the 2-month closing period would count toward your holding time, which is good if you're trying to reach that 1-year mark for long-term capital gains treatment.

You'll need at least Premier for capital gains from land sales. Deluxe won't handle Schedule D properly. I tried last year and had to upgrade mid-filing.

Thanks for saving me the headache! I'll just go straight for the Premier version then.

That's a really good point! Also, check if you're getting the same pre-tax deductions for health insurance and FSA/HSA contributions. My refund was way different one year because my new employer's health plan was $150/month cheaper, which meant $1800 more taxable income that year.

Yes, health insurance premiums are definitely something to check too! In my case, my premium went from $220 pre-tax at my old job to $180 at the new one, which added about $480 in taxable income for the year. Another thing I discovered was that my old job had automatically enrolled me in commuter benefits that took about $100/month pre-tax, and my new job didn't have that program. Small differences like these can really add up and affect your withholding and final tax bill.

You know what, this might be part of it too! My previous job did include some overtime during our busy season, maybe 3-4 hours a week for about 2 months. My new position is strictly 40 hours. That combined with the W-4 changes everyone mentioned probably explains the difference. Thanks for pointing this out - I hadn't even considered the overtime factor.