Has anyone tried just asking your employer for a simple letter stating how much you earned? I did this once when my employer "forgot" to send a 1099. I still reported the income correctly, attached the letter as documentation, and never had any issues. Sometimes a simple solution works best!

This is exactly why I keep meticulous records of all my side work - bank deposits, payment app screenshots, even text messages about payment amounts. Your employer is definitely breaking the law by not issuing a 1099 for $2,700, but that doesn't get you off the hook for reporting it. I'd suggest gathering whatever documentation you do have (bank statements showing deposits, any written communication about payments, etc.) and reporting the income on Schedule C. The IRS actually prefers when taxpayers are proactive about reporting income, even without official forms. You might also want to file Form SS-8 to get an official determination of whether you were actually an employee (in which case they should have been withholding taxes) or truly an independent contractor. Don't let your anxiety paralyze you - unreported income is way riskier than reporting income without perfect documentation. The IRS has gotten much better at tracking electronic payments in recent years, so there's a good chance they already know about this income anyway.

Don't forget to also check if what you're selling is actually taxable in each state. For example, clothing is tax-exempt in some states but taxable in others. Digital products have their own weird rules too. The nexus threshold isn't the only thing to consider...

Great question! You're mostly correct about economic nexus thresholds - staying under $100k in sales or 200 transactions typically means you don't need to collect sales tax in most states. However, there are a few important things to keep in mind: 1. **Home state physical nexus**: You'll still need to collect sales tax for customers in your home state regardless of your sales volume, since you have physical presence there. 2. **Etsy handles most of it**: Since you're selling on Etsy, they actually collect and remit sales tax for you in most states under marketplace facilitator laws. This is a huge advantage and simplifies things significantly. 3. **Keep records**: Even though you're under the thresholds now, it's good practice to track your sales by state so you'll know when you're approaching any limits if your business grows. 4. **Product taxability**: Handmade jewelry is generally taxable, but it's worth double-checking your specific state's rules since some have exemptions for certain handcrafted items. At your expected sales volume of $2,500-3,000, you're definitely safe from economic nexus in other states. Just make sure you understand your home state's requirements for small sellers - some states have minimum thresholds or simplified processes for micro-businesses.

Don't forget about the "die" part of this strategy lol. Make sure you have proper estate planning with a good attorney who understands step-up basis rules. My father-in-law did this for years but didn't update his trust after the 2017 tax law changes, and it created a mess for the family to untangle after he passed. I think this strategy makes the most sense for people in their 50s+ who have substantial appreciated assets and are unlikely to need to sell them during their lifetime. For younger investors, the benefit is less clear since the time horizon until the "die" part means decades of interest payments.

I've been implementing a modified version of this strategy for the past 3 years, and it's been working well so far. One thing I haven't seen mentioned yet is the importance of having multiple credit facilities to reduce concentration risk. I use a combination of portfolio margin loans and securities-based lines of credit from different brokers. The key lesson I learned is to always stress-test your leverage ratios against worst-case scenarios. I maintain detailed spreadsheets modeling what happens to my loan-to-value ratios under various market conditions (2008-level crash, interest rate spikes, etc.). This helped me realize I needed to keep my overall leverage much lower than I initially planned. Also, consider the psychological aspect - watching your portfolio fluctuate while carrying significant debt can be stressful. Make sure you're truly comfortable with the risk before going all-in. The tax benefits are real, but they're not worth losing sleep over potential margin calls.

I used to work at a camper dealership, and we would keep records of all manufacturer incentives paid to our salespeople. Ask your husband to talk to whoever handles the payroll or accounting at his dealership. They should have a record of all spiffs and incentives paid by each manufacturer throughout the year, even if those payments didn't come directly through the dealership. We did this specifically to help our sales staff at tax time, since manufacturer incentives can be a recordkeeping nightmare!

I'm dealing with a similar situation right now! My brother sells motorcycles and gets these manufacturer bonuses that are really inconsistent with how they're reported. Some come on his W-2, others on separate 1099s, and some seem to fall through the cracks entirely. One thing that helped us was creating a simple spreadsheet throughout the year tracking every incentive he receives - date, manufacturer, amount, and type (cash, gift card, etc.). Even if you start this now for next year, it'll save you so much stress. For your current situation, I'd definitely recommend the advice others gave about checking with the dealership's accounting department first. If that doesn't work, you might want to estimate and report the income rather than risk filing without it. The IRS is generally more understanding if you make a good faith effort to report income, even if the amount is slightly off, versus not reporting it at all and having them catch it later through 1099 matching.

I went through almost the exact same situation last year with my father's trust. The rental car expenses were driving me crazy (no pun intended) because I wasn't sure how to handle them tax-wise. What I learned from my CPA is that you're absolutely right to be concerned about proper documentation. The IRS doesn't care how much you spend on legitimate trust expenses as long as you can justify them as necessary for trust administration. In my case, I had about $7,200 in rental expenses over 10 months because the trust properties were scattered across three counties and my personal car wasn't reliable for that much driving. The key things that saved me: 1) I kept every single rental receipt with notes about what trust business I conducted each day, 2) I made sure the trust's accounting clearly showed expense reimbursements separate from my trustee fees, and 3) I documented why rental was necessary (extensive travel, need for reliable transportation for property inspections, meetings with multiple attorneys/real estate agents). The good news is these reimbursements definitely aren't taxable income to you personally - they're just the trust paying you back for money you advanced on its behalf. But definitely get them into the formal trust accounting ASAP. Even with a cooperative beneficiary, proper documentation protects everyone and is usually required by state law anyway.

I'm dealing with a very similar situation as trustee for my grandmother's estate, and this thread has been incredibly helpful! One thing I'd add from my recent experience is to make sure you understand your state's specific trust accounting requirements early on. In my state (Colorado), I discovered that trustees are required to provide annual accountings to beneficiaries that clearly separate trustee compensation from expense reimbursements. I wish I had known this from the beginning because I had been lumping everything together in my informal tracking. For the car rental situation specifically, what helped me was creating a simple spreadsheet with columns for: Date, Rental Period, Trust Business Conducted, Miles Driven, and Total Cost. This made it really easy to show the connection between each rental expense and specific trust administration activities when I prepared my formal accounting. Also, don't forget that some rental car insurance and gas costs might also be reimbursable trust expenses if they were incurred for trust business. I initially thought I could only claim the base rental cost, but my attorney confirmed that reasonable associated expenses are typically covered too. The peace of mind from having everything properly documented is worth the extra effort upfront!