Has anyone tried using a payment app like Venmo or Cash App for these private seller transactions? I'm wondering if the digital receipt from that would be sufficient documentation.

Great question! As someone who's been running a small carpentry business for 3 years, I can share what's worked for me. You definitely need documentation for all business expenses, even from private sellers. Here's my system: I created a simple receipt template on my phone that I fill out on the spot. It includes: seller name, contact info, date, detailed description of materials (species, dimensions, quantity), purchase price, and payment method. I have the seller sign it if they're willing, take a photo of the materials, and note the intended business use. For sellers who won't sign anything, I still document everything I can and take timestamped photos. I also photograph my cash withdrawal receipt if I paid cash, which creates a paper trail. The IRS wants to see that you have adequate records to substantiate your business expenses. Consistency is key - use the same documentation method every time. I keep all my receipts (both formal and self-created) organized by month in both physical and digital folders. One tip: if you're buying expensive specialty wood, consider bringing a witness who can verify the transaction if the seller is hesitant about paperwork. This has helped me a few times with valuable hardwood purchases from estate sales.

As someone who's been reselling on various platforms for about 2 years, I can definitely confirm that phone deductions are legit! I upgrade my phone every couple years specifically because I need good camera quality for listing photos and a fast processor for managing inventory apps. One thing I learned the hard way - make sure you're also deducting things like your phone case and any accessories that help with business. I have a tripod mount and ring light attachment that I use exclusively for taking product photos, and my accountant said those are 100% deductible as business equipment. Also, regarding your monthly phone bill question - you're absolutely right that it's separate from your home office deduction. I've been deducting about 70% of my monthly bill based on my usage patterns, and it adds up to a nice chunk of savings over the year. The key is just being consistent with whatever percentage you choose and having a reasonable way to back it up if asked. Good luck with the new phone - having better tools really does make the business more efficient!

Great question about phone deductions! I've been doing eBay reselling for about 4 years and can confirm this is totally legitimate. Your 60% business use estimate sounds reasonable - I actually use about 70% for my reselling business. One tip that's saved me headaches: I keep a simple monthly log where I note my business vs personal usage pattern. Nothing fancy, just "approximately 70% business use this month - heavy listing activity, customer messages, and inventory scanning." Takes 2 minutes but gives me documentation if needed. For the phone purchase itself, you can either take the full business percentage as a Section 179 deduction in year one, or depreciate it over time. Most small sellers I know prefer the immediate deduction since cash flow matters more than spreading it out. And yes, definitely start deducting your monthly phone bill! It's completely separate from home office expenses. I've been deducting the business percentage of my monthly bill for years - it adds up to several hundred dollars in deductions annually. The IRS expects mixed-use items for small businesses, so don't stress too much about having the "perfect" percentage. Just be reasonable and consistent with whatever method you choose for calculating business use.

The reciprocity agreement information is really valuable! Since you mentioned Illinois specifically, I can help clarify: Illinois has reciprocity agreements with Iowa, Kentucky, Michigan, and Wisconsin. This means if you're an Illinois resident who worked in any of these states (or vice versa), you typically only file in your state of residence. However, since you've established legal residency in Illinois through voter registration and driver's license, you'd file there as a resident regardless. The reciprocity would help if you had summer income from Wisconsin, Iowa, Kentucky, or Michigan - you'd only need to file the Illinois return. For tax software, I'd definitely recommend going that route for multi-state situations. TurboTax, FreeTaxUSA, and H&R Block all handle this really well. They'll ask you questions like "Did you live in more than one state?" and "Did you earn income in multiple states?" then guide you through each state's requirements. Much less overwhelming than trying to figure it out manually! One thing to keep in mind - even if you end up needing to file in both states, you're not necessarily paying double tax on the same income. The resident state (Illinois in your case) will give you a credit for taxes paid to the non-resident state, so you're only paying the higher of the two tax rates.

Just went through this exact situation last year as a college student! The key thing that helped me was understanding that tax residency and legal residency aren't always the same thing. Since you've established legal ties in your college state (voter registration + driver's license), most states would consider you a resident for tax purposes. But here's what I wish someone had told me earlier - call both state tax departments directly to confirm your specific situation before filing. I spent weeks reading conflicting information online, but a 10-minute call to each state's taxpayer services line gave me definitive answers. They can tell you exactly what your filing requirements are based on your specific circumstances. Also, don't stress too much about "getting in trouble" - if you make a good faith effort to file correctly and make an honest mistake, both states have processes to help you fix it. The penalties for genuine errors by students are usually pretty minimal, especially for first-time filers. One last tip: keep detailed records of where you earned each dollar this year. It makes the whole multi-state filing process much smoother, whether you end up needing to file in one state or both.

Great question about CDL training deductions! I went through something similar when I got my CDL last year. The key thing to understand is that since the Tax Cuts and Jobs Act, most employee education expenses can't be deducted directly anymore, but you still have options. For your $5,100 CDL training, you'll likely want to look into the Lifetime Learning Credit since it sounds like you're working as an employee driver rather than being self-employed. This credit can give you up to $2,000 back (20% of the first $10,000 in qualified education expenses), and vocational training like CDL programs typically qualify. Make sure to keep all your receipts and documentation from the training program - you'll need Form 8863 to claim the credit. Also double-check the income limits for the credit based on your filing status. If you end up going the owner-operator route in the future, then you could potentially deduct similar training costs as business expenses on Schedule C. The mandatory nature of the ELDT requirement actually works in your favor here since it demonstrates the training was necessary for your profession. Definitely worth exploring the Lifetime Learning Credit route!

This is such a timely question! I just went through this exact situation when I got my CDL through an ELDT program earlier this year. The mandatory nature of the training definitely makes it frustrating that we can't take a straight deduction anymore. One thing I'd add to the great advice already given here is to make sure you get Form 1098-T from your training school if they issue one. Not all CDL schools provide these forms, but if yours does, it makes claiming the Lifetime Learning Credit much smoother during tax filing. The form shows exactly what you paid for qualified tuition and fees. Also, if you're planning to work as an employee driver initially but might go owner-operator later, keep detailed records of everything. If you do transition to being self-employed within a reasonable timeframe, you might be able to argue that the training was a startup business expense, which could be more beneficial than the credit depending on your tax situation. The income limits for the Lifetime Learning Credit can be tricky too - they're based on your modified adjusted gross income, so if you're right on the border, it might be worth timing when you file or considering other income adjustments to stay within the qualifying range.

Anyone using tax software to handle this? I tried using TurboTax but it's still confusing me with how it imports the 1099-B and then what goes where.

As someone who's dealt with Schedule D and Form 8949 for several years now, I'd recommend double-checking your broker statements against what you report. Sometimes brokerages make errors on the acquisition dates or cost basis, especially if you transferred stocks between accounts. For your 6-month holding period stocks with $3,200 in profits, you're definitely dealing with short-term capital gains (taxed as ordinary income). Make sure each transaction on Form 8949 Part I matches exactly what's on your 1099-B forms - the IRS computer system will flag any discrepancies. One tip: if you have a lot of transactions, consider grouping identical securities with the same acquisition and sale dates on a single line of Form 8949, rather than listing each share lot separately. This keeps the form cleaner while still being compliant. Also, don't forget that short-term gains are added to your regular income for tax purposes, so depending on your tax bracket, you might owe more than you expect. Worth setting some money aside if you haven't already!