One major thing nobody's mentioned yet is sales tax nexus. Even without physical presence, many states now have economic nexus laws after the South Dakota v. Wayfair case. You'll likely need to collect and remit sales tax in states where you exceed certain thresholds (usually $100k in sales or 200 transactions). Given your international setup, you should really budget for a good sales tax compliance software from day one. TaxJar or Avalara aren't cheap but they're way cheaper than getting hit with penalties later. Delaware and Florida are pretty similar here - your sales tax obligations depend on where your customers are, not where you incorporate.

Great question! I went through this exact decision process for my SaaS startup last year as a non-US founder. Here's what I learned: **Delaware vs Florida for your situation:** Since you won't have physical presence in either state, you're looking at franchise taxes as the main difference. Delaware charges an annual franchise tax (minimum $175-400 depending on method), while Florida has no franchise tax but charges an annual report fee (~$139). **Entity choice recommendation:** For international e-commerce with growth plans, I'd strongly recommend Delaware C-corp. Here's why: - Clean separation between personal and business taxes (crucial for international founders) - Investor-ready if you ever want to scale - Well-established legal framework for disputes - Most US banks and payment processors are familiar with Delaware corps **Hidden taxes to watch:** - Sales tax nexus in customer states (this is huge - budget for compliance software early) - Customs duties and import taxes (varies by product classification) - Potential state income tax in states where you have employees later - GILTI tax on foreign-controlled US corporations (if you own >50%) **Banking tip:** Mercury and Brex both work well with Delaware corps and foreign founders. Start the banking process early - it takes longer for international owners. The state choice matters less than getting your sales tax and import duty strategy right from day one. Those will likely be your biggest ongoing tax obligations.

Don't forget about COMMUTING miles vs BUSINESS miles. This tripped me up my first year with an S corp. The miles from your home to your primary business location are considered commuting and are NOT deductible, even with an accountable plan. Only miles from your office to client locations, between different work sites, or for other business purposes can be reimbursed. I lost about 30% of my claimed mileage last year because I incorrectly included commuting miles in my reimbursement request. Had to amend returns and it was a huge headache.

One thing I'd add to this great discussion - make sure you're properly documenting the BUSINESS PURPOSE for each trip, not just the mileage. The IRS requires more than just "business meeting" in your records. For each business trip, you should document: - Date and time - Starting and ending locations with addresses - Business purpose (specific client name, type of meeting, etc.) - Total miles driven - Any personal stops (which you'd subtract from business miles) I learned this the hard way during an audit a few years ago. The IRS agent wasn't satisfied with generic entries like "client meeting" - they wanted to see "Meeting with Johnson Construction to discuss Q1 project timeline" or "Picked up materials for Smith renovation at Home Depot." Also, since you mentioned using Gusto for payroll, they have expense reporting features that can help you track and submit mileage reimbursements properly. You can set up recurring monthly submissions so you don't have to do everything at year-end like you're planning for this year. Good luck with your first year as an S corp!

Has anyone successfully disputed a PayPal 1099-K? Mine shows about $35k but a lot of that was just money moving between my own accounts.

I'm dealing with a very similar situation - got a 1099-K from PayPal for around $78k, mostly from moving money between sportsbooks and some peer-to-peer transfers with friends for betting. Like you, I'm definitely at a net loss for the year. One thing I learned is that you absolutely need to address this on your return even if most transactions weren't actual income. The IRS computer systems will flag the discrepancy between your 1099-K and what you report as income, potentially triggering an audit or CP2000 notice. I'd definitely recommend going with a CPA over H&R Block for this. The CPA I consulted explained that with gambling transactions, you need to be very careful about how you categorize everything. They helped me understand that transfers between accounts aren't income, but any actual gambling winnings are - even if offset by losses. Make sure you get year-end statements from all your sportsbooks showing your net win/loss. Most platforms like DraftKings, FanDuel, etc. provide these for tax purposes. This documentation will be crucial if the IRS has any questions about your return. The peace of mind of having it done correctly is worth the extra cost of a CPA, especially with this much money involved.

Anyone else think its crazy that in 2023 were still dealing with paper checks and snail mail for tax refunds? The whole system needs an overhaul smh

I had the exact same thing happen to me last year! What worked for me was filing Form 3911 (Taxpayer Statement Regarding Refund) - you can download it from the IRS website. It's specifically designed for this situation. Fill it out completely and mail it with copies of your ID and proof of your new address. I got my replacement check about 6 weeks later. Way faster than just writing a letter, and it goes directly to the right department. Hope this helps!

Does your 806 code have a specific cycle date associated with it? The cycle date can sometimes indicate when your return is being processed in the IRS weekly cycles, which might give you insight into your refund timing.

I had the exact same concern when I first saw code 806 on my transcript! As others have mentioned, it's simply your withholding credits - nothing to worry about at all. Since you mentioned you've been preparing your own returns since retiring in 2018, you might find it helpful to know that code 806 has likely been on all your previous transcripts too, but it's easy to overlook if you're not specifically looking for it. The amount should match your total federal withholding from all your income sources (W-2s, 1099s with backup withholding, estimated payments, etc.). Your 17-day wait is still well within the normal 21-day processing window, so you should see movement soon!