Quick tip - many states have marketplace facilitator laws now which means platforms like Etsy, Amazon, and eBay are required to collect and remit sales tax on your behalf regardless of whether you have nexus. This covers about 40+ states now. But be careful! If you sell on your own website or multiple channels, you still need to track your total sales across ALL platforms to determine nexus. The marketplace might handle collection for their platform sales, but they don't know what you're selling elsewhere.

As someone who went through this exact same confusion when I started my online business, I totally get your overwhelm! The good news is it's not as scary as it seems once you understand the basics. Since you're based in Arizona, you definitely need to collect sales tax there. For other states, you only need to worry about it once you hit their economic nexus thresholds (usually $100k in sales OR 200+ transactions per year in that state). Here's what I wish someone had told me when I started: 1. Check if Etsy is already handling sales tax collection for you in most states (they probably are!) 2. Keep detailed records of your sales by state - you'll need this info 3. Don't panic about registration until you actually hit thresholds 4. Consider using sales tax software once you start selling in multiple states The key is to stay organized from the start. I use a simple spreadsheet to track my monthly sales by state so I know when I'm approaching any thresholds. Most small businesses don't hit nexus requirements in multiple states right away, so you likely have time to figure this out properly. Focus on growing your business first - just make sure you're collecting Arizona sales tax and keeping good records. The rest will become clearer as your sales grow!

I had this issue last year and learned the hard way that issuing duplicate 1099s is a HUGE headache. One of my contractors got audited because Stripe reported $12,400 and I also reported $12,400 so it looked like they made $24,800 to the IRS. That contractor had to spend hours proving it was duplicate reporting.

This is exactly the kind of situation that trips up small business owners! I faced something similar with my landscaping business. Here's what I learned after consulting with my CPA: The golden rule is: never double-report the same payment. If Stripe is issuing 1099-NECs to your contractors (which they do for amounts over $600), then you should NOT include those payments on your own 1099s. Here's my recommended approach: 1. Log into your Stripe dashboard and check their tax reporting section - it should show you which contractors will receive 1099s from them 2. For QuickBooks, continue tracking everything for your own records, but when generating 1099s, exclude the Stripe payments that Stripe is already reporting 3. Only issue 1099s for Venmo payments (assuming you're using personal Venmo - if it's Venmo Business over $600, they'll also issue forms) I also keep a simple spreadsheet that breaks down each contractor's total payments by platform. This makes it crystal clear at tax time what needs reporting from me versus what's handled by the payment processors. The peace of mind is worth the extra record-keeping effort - trust me on this one!

I went through this same situation two years ago when I switched jobs mid-year. One important detail that hasn't been mentioned yet - make sure you get the corrective distribution processed before December 31st of the year following your over-contribution if possible. While you technically have until April 15th to request the return of excess, getting it done in the same calendar year can simplify your tax situation. The earnings on the excess contribution will be taxable in the year the distribution actually occurs, not necessarily when you originally made the over-contribution. Also, keep detailed records of all your communications with your plan administrator. I had to follow up multiple times before mine actually processed my request. Don't let them brush you off - you have the right to correct this error and they're required to help you do it properly. The good news is this won't trigger an audit as long as you handle it correctly. The IRS sees these corrective distributions all the time, especially during job change seasons.

This is such a stressful situation but you're definitely not alone! I dealt with a similar over-contribution issue when I switched jobs in the middle of last year. The key thing is to act quickly since you still have time to fix it properly. From my experience, your best bet is to contact the 401k plan administrator directly (not just HR) at your current employer where the excess contribution is sitting. Most major providers like Fidelity, Vanguard, or Charles Schwab have dedicated lines for these situations. When you call, specifically ask for a "corrective distribution" or "return of excess contribution" for 2025. They'll need to calculate not just the $1,500 excess, but also any earnings (or losses) on that amount from when it was contributed until when it's distributed back to you. This whole amount becomes taxable income for 2025, but you avoid the much worse 6% annual excise tax that kicks in if you don't fix it. Don't let your HR department's unhelpful response discourage you - the plan administrator is legally required to process these corrections and they deal with them regularly. Get it done before April 15, 2026 and you'll be in good shape!

I went through a very similar situation last year with my S-corp and COBRA premiums. The key thing that helped me was getting everything documented properly from the start. Here's what I learned: Yes, you can absolutely deduct the full $39,000 in COBRA premiums as a self-employed health insurance deduction, but the process matters. Your S-corp needs to reimburse you for those premiums you paid out of pocket (make sure this happens before December 31st). The reimbursement gets added to your W-2 income in Box 1 but not Boxes 3 and 5. For documentation, I created a simple board resolution stating that the company would reimburse health insurance premiums for employees. I kept copies of all my COBRA payment receipts, the reimbursement check from my business account, and a memo explaining the reimbursement. My CPA said this was more than sufficient. The amount might seem large, but it's a legitimate business expense. I claimed about $32,000 last year with no issues. Just make sure your accountant codes everything correctly on your W-2 and that you claim the deduction on Schedule 1 of your 1040, not as an itemized medical expense. One tip: If you're switching to ACA coverage when COBRA ends, you can handle those premiums the same way going forward.

This is exactly the situation I was in two years ago! The confusion you're experiencing is totally understandable because the rules for S-corp owners are different from sole proprietors, and not all tax professionals are familiar with the specifics. You're absolutely right that you can take the full deduction for your COBRA premiums. The process everyone outlined above is correct - have your S-corp reimburse you for the $39,000 you paid out of pocket, include it in your W-2 Box 1 income (but not FICA wages), then claim the self-employed health insurance deduction on your personal return. One thing I'd add that helped me sleep better at night: I also kept a spreadsheet tracking each monthly COBRA payment with dates, amounts, and confirmation numbers. When my S-corp reimbursed me, I referenced this spreadsheet in the memo line of the reimbursement check. It created a clear paper trail showing the business purpose of the reimbursement. The second accountant who told you COBRA doesn't qualify was simply wrong - there's no distinction in the tax code between regular health insurance and COBRA continuation coverage for this deduction. Don't let that bad advice cost you thousands in legitimate tax savings! Make sure to get this reimbursement processed before December 31st, and you'll be in great shape for your 2024 taxes.

I went through this exact nightmare two years ago and it was absolutely maddening! The key thing that finally worked for me was getting everything in writing and being incredibly persistent with the right documentation. Here's what I learned: When your check gets processed as ACH (which happens automatically with most banks now), the IRS systems sometimes can't match it back to your account because the electronic processing strips away some of the identifying information from the original paper check. What finally resolved it for me was calling the IRS and specifically asking for a "Manual Research Request" in addition to the payment tracer. This is different from a regular payment tracer - it's when they have a human manually search their database using multiple criteria (your SSN, the exact amount, the date range, etc.). Also, make sure you ask them to check their "Unpostable Transaction" file. Sometimes payments end up there when the system can't figure out where to apply them. I wish someone had told me about this sooner - my payment was sitting in that file for three months! The whole process took about 8 weeks, but once they found it, they not only applied the payment but also removed all the penalties and interest that had accumulated. Keep fighting - you paid that money and they will find it eventually!

I work as a tax resolution specialist and see cases like this regularly - you're definitely not alone! The issue you're experiencing happens when paper checks get converted to ACH payments by the banking system, which can cause the payment to lose some identifying information that the IRS needs to properly credit your account. Here's my recommended action plan: 1. **Gather your documentation**: You'll need your bank statement showing the deduction, the ACH trace number, and the exact date/amount of the transaction. 2. **Call the IRS and use specific language**: Ask for a "payment tracer for an ACH transaction" - NOT just "missing payment." Also request they check their "Unpostable Transaction file" as payments sometimes get stuck there when the system can't determine where to apply them. 3. **Request account protection**: Ask them to place a "pending payment marker" on your account to stop additional interest from accumulating while they search. 4. **Get everything documented**: Ask for a confirmation number for the payment tracer and get the representative's name/ID number. If the first representative can't help with these specific requests, politely end the call and try again - different reps have varying levels of experience with payment traces. As a backup plan, consider visiting a local Taxpayer Assistance Center for in-person help, or contact the Taxpayer Advocate Service at 1-877-777-4778 if phone attempts continue to fail. The good news is that once found, they typically remove any incorrectly assessed penalties and interest. Stay persistent - your payment is in their system somewhere!