As someone who's made ISO mistakes before, I strongly recommend keeping a spreadsheet with all your grant dates, exercise dates, fair market values, and exercise prices. It's easy to lose track, especially if you have multiple grants or partial exercises. Also, don't forget about state taxes! Everyone focuses on federal, but states have different rules for how they treat ISO dispositions.

This is such a timely discussion! I just went through this exact situation last month. One thing that really helped me was understanding that the "disqualifying disposition" ordinary income treatment only applies to the spread at exercise, not the entire gain. So in your case, Mateo, if you sell now for $42,000 and you paid $12,000 for shares worth $35,000 at exercise, here's what happens: - The $23,000 spread at exercise becomes ordinary income (taxed at your regular income rate) - The additional $7,000 gain ($42,000 - $35,000) is treated as short-term capital gains This is different from a qualifying disposition where the entire $30,000 gain ($42,000 - $12,000) would be long-term capital gains. Also, don't forget you may have already triggered AMT liability when you exercised in March 2024, regardless of whether you sell now or later. That $23,000 spread was an AMT preference item in 2024. The decision really comes down to: pay ordinary income rates on $23,000 now + short-term capital gains on $7,000, versus waiting and potentially paying long-term capital gains rates on the full $30,000 (assuming the stock price holds).

My mom tried one of those big chain tax prep places for her retirement planning and they totally missed some important deductions related to her medical expenses. Cost her hundreds. Just make sure whoever you hire actually specializes in retirement tax issues specifically - not all "tax pros" are created equal!

I made the switch to a tax specialist two years ago when I started dealing with multiple retirement accounts and some stock options from my previous employer. The complexity threshold for me was when I realized I was spending entire weekends researching tax implications instead of just filing my return. My CPA has been worth every penny - she's caught things like optimal timing for Roth conversions based on my income projections, and helped me understand how to coordinate withdrawals from different account types to minimize my overall tax burden. She also set up a multi-year tax strategy that I never would have thought of on my own. The peace of mind is huge too. I sleep better knowing someone who does this full-time is handling the complex stuff, and I can focus on the actual retirement planning rather than worrying about tax mistakes. From your post, it sounds like you're definitely at that complexity threshold. I'd recommend getting a consultation - most good tax pros will give you an initial assessment of your situation and whether their services would be beneficial.

Make sure to also check if you need an ITIN (Individual Taxpayer Identification Number) or EIN (Employer Identification Number) for your business. You'll definitely need one of these to file any US tax forms.

As someone who went through this exact process last year with my international marketplace, I'd strongly recommend getting professional help rather than trying to handle this yourself. The compliance requirements are incredibly complex and change frequently. Beyond what others have mentioned, you'll also need to consider: 1. **Information reporting requirements** - You may need to file Forms 1099-K for US vendors who exceed certain payment thresholds ($600 for 2024) 2. **Backup withholding** - If vendors don't provide proper tax documentation (W-9 forms), you might need to withhold 24% of their payments 3. **State economic nexus laws** - These vary significantly by state and some have very low thresholds (South Dakota is just $100K in sales OR 200 transactions) 4. **Treaty benefits** - Depending on your home country, you might be able to reduce or eliminate certain US tax obligations through tax treaties The penalty structure is also quite severe - states can impose penalties of 25% or more of uncollected taxes, plus interest. For a growing business, getting this wrong upfront can be financially devastating. I'd recommend starting with a comprehensive analysis of your specific situation before making any moves. The investment in proper guidance upfront will save you significantly more in penalties and corrections later.

Has anyone had experience with renting out their timeshare when not using it? I've heard you can deduct more expenses that way, but I'm not sure about the rules. Thinking about doing this with our new timeshare to offset some costs.

Just to add another perspective - I went through something similar when I bought my cabin in late December. The key thing to remember is that you can only deduct property taxes that were actually paid during the tax year, not just accrued. So if the property taxes for the full year were paid by the previous owner and you reimbursed them at closing, you can only deduct the portion that covers your 3-day ownership period. Also, make sure to keep your HUD-1 settlement statement or closing disclosure - it should show exactly how the property taxes were prorated. This will be your documentation if the IRS ever questions the deduction. The amount will be tiny for just 3 days, but it's still legitimate if you decide to itemize. One more thing - if you're close to the standard deduction threshold, those few days of property taxes might not be worth itemizing for. Sometimes it's better to just take the standard deduction and save yourself the paperwork hassle.

Think of the IRS verification process like airport security. Some people get randomly selected for additional screening, others get flagged for specific reasons. Just like TSA PreCheck can speed you through airport security, having properly documented business expenses and clean record-keeping can reduce your chances of verification holds in future years. My verification took 14 days to process last year, but this year I had no verification requirements because I improved my documentation.

Great question Dylan! I went through phone verification last year and it took exactly 16 days after my call for the refund to hit my account. The key thing I learned is that the IRS processes verifications in batches, usually on Tuesdays and Fridays, so timing matters. I called on a Wednesday and my transcript updated the following Friday showing the verification was processed. Then it took another 10 days for the actual refund deposit. One tip - after you verify, check your transcript weekly rather than daily since updates typically happen on those batch processing days. Also keep your confirmation number from the verification call handy in case you need to follow up.