Quick tip on the PayPal/1099-K situation - PayPal is required to issue 1099-Ks for annual payments over a certain threshold, but that doesn't mean you have to pay taxes twice! When I enter my tax info, I always: 1) Enter the 1099-NEC first 2) When TurboTax asks about 1099-K, I say yes, I received one 3) When it asks if this income was already reported elsewhere, I say YES 4) It'll then ask you to identify which income it duplicates This way everything is properly documented but not double-counted. Hope that helps!

Based on your situation, here's what I'd recommend: **For the teaching income ($1,875.50):** You're absolutely right to only report this once. Use the 1099-NEC from the makerspace and ignore the PayPal 1099-K for the same payments. **For the $31.75 reimbursement:** This shouldn't be included as income since it was reimbursement for out-of-pocket expenses you incurred for the classes. You can subtract this from your total income, but then you also can't claim those material costs as expenses. **For the $25 hobby sale:** Unfortunately, yes, you need to report this as "Other Income" even though you lost money overall. The elimination of hobby expense deductions really stings in situations like yours. **Consider the business angle:** Given that you teach classes regularly at the makerspace, keep records, and have expertise in woodturning, you might actually qualify to treat this as a business rather than a hobby. This would let you use Schedule C and deduct your teaching-related expenses against your income. The key is showing profit motive - even if you're not profitable yet, if you're operating in a businesslike manner, it could qualify. I'd suggest talking to a tax professional about whether your teaching activities meet the business criteria. It could save you money and better reflect the reality of what you're doing.

2 Has anybody used Drake Tax for this kind of situation? My accountant uses it and claims it's the best for complex investment scenarios, but I'm wondering if it's worth switching to them from my current guy who uses Lacerte.

For high-volume traders like yourself, I'd strongly recommend considering FreeTaxUSA Deluxe. I know it doesn't get mentioned as much as the big names, but it handles complex investment scenarios surprisingly well for the price point. What sets it apart is that it properly imports broker data while preserving transaction details that other software often strips out. The wash sale calculations work across multiple brokerages, and it handles Form 8949 entries efficiently even with thousands of transactions. The real advantage is in the user interface - when you need to review or adjust imported data (which you will with that volume), FreeTaxUSA makes it much easier to navigate and edit individual transactions compared to TurboTax or H&R Block. For Form 6781 straddle reporting, it provides clear guidance and proper categorization. At $15 for the Deluxe version, it's worth trying as a backup option even if you go with something else as your primary software. You can import your data and see how it handles everything before committing to file with it.

Anyone know if getting a car loan affects how Section 179 works? I'm looking at a $45k work van but financing most of it. Can I still claim the full amount or only what I put down?

Great question about financing! You can definitely claim the full Section 179 deduction on the entire purchase price, not just your down payment. The IRS considers you to have "placed the asset in service" when you start using it for business, regardless of your financing arrangement. Just keep a few things in mind: make sure you have adequate business income to absorb the deduction (Section 179 can't create a business loss), and document that the van is used more than 50% for business purposes. Also, don't forget about the vehicle weight limits - if your van is over 6,000 lbs GVWR, you might be able to deduct more than the typical passenger vehicle limits. The financing actually works in your favor from a cash flow perspective - you get the full tax benefit upfront while spreading the actual payments over time.

The whole "billionaires don't pay taxes" thing is often misunderstood. They DO pay taxes - just not on unrealized gains (stock they haven't sold yet). Nobody pays taxes on unrealized gains. The real advantage they have is: 1) They can afford to never sell (living off loans using their stock as collateral) 2) They can time their sales perfectly for tax planning 3) If they hold until death, heirs get a stepped-up basis (meaning gains during their lifetime are never taxed) 4) They have access to sophisticated tax planning strategies and high-priced accountants For regular employees with RSUs or stock options, the best approach is usually a diversification strategy where you systematically sell company stock after vesting to reduce concentration risk, regardless of tax considerations.

This is such a common frustration, and you're absolutely right that the system feels unfair. I went through the same thing for years - watching a third of my RSUs disappear immediately to taxes while reading about billionaires paying zero. One thing that helped me was understanding that we can actually learn from some of the strategies the wealthy use, just on a smaller scale. After your RSUs vest and you've paid the income tax, any additional gains on the shares you keep are treated as capital gains (not ordinary income). If you can afford to hold onto some of those shares instead of selling everything immediately, you get similar tax treatment to what billionaires get on their holdings. I also started timing my stock sales more strategically - selling some in years when my income is lower, or pairing sales with capital losses from other investments to offset gains. It's not going to make you a billionaire, but these small optimizations can add up over time. The key difference is billionaires have enough wealth that they never NEED to sell, while we often have to sell to cover living expenses. But even keeping 20-30% of your vested shares (if financially feasible) can help you benefit from the same long-term capital gains treatment they use.

I'm really sorry for your loss. This is such a thoughtful thing you're doing for your brother during an already difficult time. The advice here about federal taxes is spot on - you won't owe income tax on the life insurance proceeds, and while you'll need to file Form 709 for the gift over $18,000, you almost certainly won't owe actual gift tax due to the high lifetime exemption. One thing I'd suggest is keeping good documentation of everything. Save records showing the insurance payout amount, when you received it, and when/how you transferred the money to your brother. If you ever get questions from the IRS down the road, having a clear paper trail will make everything much smoother. Also, since this is a substantial amount, you might want to consider consulting with a tax professional just to be extra safe, especially for filing that Form 709 correctly. Many CPAs offer consultations for a reasonable fee and it could give you peace of mind that everything is handled properly. Your brother is lucky to have someone who wants to do right by family even when they're not legally required to. Best wishes to both of you during this tough time.

First, I'm so sorry for the loss of your mom. What you're planning to do for your brother shows incredible character during such a difficult time. I wanted to add one practical tip that might help: when you do the transfer to your brother, consider doing it via wire transfer or cashier's check rather than a personal check, especially for this amount. Banks sometimes flag large personal checks and put holds on them, which could create unnecessary stress for your brother. A wire transfer or cashier's check will clear immediately and provides a clear paper trail for your records. Also, timing-wise, you don't have to rush the gift tax filing. Form 709 is due with your regular tax return (so April 15th for the year you make the gift), but if you need an extension, you can file for one. This gives you time to get organized and possibly consult with a tax professional without feeling pressured. One last thought - make sure you're emotionally ready for this decision. While it's incredibly generous, $162,500 is life-changing money. Take some time to process your grief and make sure this feels right for you in the long term. Your mom named you as the sole beneficiary for a reason, and whatever you decide to do with that money should be something you feel completely at peace with.