What about uniforms and equipment? I'm guessing my security uniform is deductible but what about boots, flashlights and that kind of stuff?

Uniforms are typically deductible if they're required for your job and not suitable for everyday wear. So generic black pants probably wouldn't qualify, but a shirt with a security company logo would. Equipment like flashlights, specialized boots, and other gear is generally deductible if it's specifically required for your security work and not something you'd use outside of work. Keep all receipts and document how each item is used specifically for work purposes. Small items under $200 can often be fully deducted in the year purchased, while more expensive equipment might need to be depreciated over several years.

I used TurboTax Self-Employed last year for my security consulting business. It does have some industry-specific questions but honestly wasn't great for the more nuanced deductions. It asked about standard business expenses but didn't really guide me through the professional development stuff. I ended up upgrading to their Live service to talk to a tax expert about my martial arts training.

Can you explain more about how you track your mileage? I've been using a paper logbook but it's getting to be a pain. Is there an app you recommend that's IRS-compliant?

I use MileIQ for tracking all my business drives. It runs in the background on my phone and automatically detects when I'm driving. At the end of each trip, I just swipe right for business or left for personal. It creates IRS-compliant reports with timestamps, routes, mileage, and purpose fields. Before that, I tried Everlance and Stride, which are also good options. The key is finding one that's automatic enough that you'll actually use it consistently. The IRS wants to see regular documentation throughout the year, not something you created all at once at tax time. Whatever system you choose, make sure it captures date, starting point, destination, purpose of trip, and miles driven.

That sounds terrifying. Did you have to pay penalties or just the additional tax? I'm wondering how aggressive they are with these vehicle deduction issues.

Thanks for the tip! My dad gets a small social security check ($843/month) but it all goes toward his medications that aren't covered by Medicare. Would that count against the income limit? And yes, I've been keeping all receipts for household expenses since I had a feeling this might come up.

Social Security benefits do count toward the gross income test for dependency, so that's about $10,116 annually. For 2024, the gross income limit for dependents is $4,700, so your father's income is over that threshold. However, there's still a way you might qualify for head of household. Even if your father doesn't meet the gross income test to be your dependent, he might still be considered your "qualifying relative" for head of household purposes if you provide more than half his support and he meets the other tests. This is a special exception specifically for parents. Keep documenting everything - especially showing how his SS income is spent entirely on his medical needs and how you cover everything else.

That's really helpful to know! My mom lives in her own apartment but I pay for everything. I've been filing as single all this time... wonder if I should amend my past returns?

Do you know if I could pay just enough to get under the $10k threshold and then set up a payment plan for the remainder to avoid the lien? Would that work?

Yes, that strategy can work! If you can pay enough to get your balance under $10,000 before you set up the installment agreement, you'll significantly reduce the chances of the IRS filing a lien. In your case, since you owe about $12k, you could pay around $2-3k upfront and then immediately request an installment agreement for the remaining balance. Make sure to get confirmation that the payment has been applied before you request the installment agreement. This approach isn't guaranteed to prevent a lien in all cases, but it follows their general guidelines and works in many situations.

Yes, you can absolutely still request penalty abatement even after receiving a CP504! The First Time Abatement (FTA) program applies regardless of what stage of collections you're in, as long as you meet the criteria: good compliance history (no significant penalties) for the three tax years prior to the year you received penalties. You'll want to call the IRS or include Form 843 with your request. I've seen numerous clients successfully get penalties removed even after receiving CP504 notices. Just make sure to address the underlying tax debt too, either by paying it or setting up an installment agreement.

Do student loans really count as the student providing their own support? I thought since they're loans that need to be paid back later, they wouldn't count for the current tax year?

Yes, student loans absolutely count as support provided by the student for the current tax year, regardless of when they'll be repaid. The IRS looks at who paid the expenses during the tax year, not where the money originally came from. Even if your parents cosigned the loans, as long as you're legally obligated to pay them back, the tuition and expenses paid with those loan funds count as support you provided for yourself. The same applies to scholarship funds - those count as support you provided (not support from your parents), even though the money comes from a third party.

The IRS actually contacted you both about this? How long did it take for them to notice the duplicate dependency claim?

It happened pretty fast! We both filed in February, and by April we each got letters asking for documentation. The duplicate dependency claim triggered an automatic flag in their system. The IRS actually put both of our refunds on hold until the issue was resolved. My parents had to pay back the extra refund they received from claiming me plus a small penalty. The whole process took about 3 months to resolve completely. Definitely not something you want to deal with during finals or job hunting!