That's an interesting angle I hadn't considered. How exactly would I document it as a loan at this point? We've already processed the reimbursement as a regular transfer from the business account to my personal account a few months ago.

You'd need to create a promissory note between yourself and the company, with reasonable interest terms (look up the applicable federal rate for the time period), and have your board of directors (even if that's just you) approve it retroactively. Then reclassify the "reimbursement" payment as loan repayment in your books. Be aware that this approach works best if the amount was clearly definable and specific, like covering exact payroll amounts. If you've been mixing personal and business expenses regularly without clear documentation, this becomes much harder to justify. Also, don't forget to include any interest required on the loan when doing your taxes - even if you choose to forgive it, there can be tax implications.

This is a really good point. What type of business entity do you have, OP? The tax treatment can vary significantly based on whether you're running an S-corp, C-corp, sole prop, etc.

That's interesting! My vintage business will be expanding to sell some digital patterns soon. Do you know if downloadable sewing patterns would be taxable in Colorado? Or would they count as a non-taxable service?

Digital products in Colorado are generally taxable if they're considered "tangible personal property" in electronic form - like downloaded patterns, designs, etc. However, custom design work or services are usually exempt. For your sewing patterns, they would likely be considered taxable digital goods in Colorado since they're standardized products rather than custom services. But other states vary wildly on digital taxation - some exempt all digital products while others tax everything. The rules change constantly too, which makes compliance a huge headache for businesses like ours.

I've been using TaxJar for about 2 years and it's decent but not perfect. It sometimes gets special district taxes wrong in Colorado which then requires manual adjustments. If you're only selling in a few states it might be overkill. Avalara is more comprehensive but also more expensive.

I'm fairly certain mine are all after-tax since I'm paying directly from my personal bank account each month. But is there a way to verify this for sure? The premiums went up significantly after retirement compared to when I was working.

The significant increase you're seeing is common. While employed, employers often subsidize a large portion of premiums or you may have been paying with pre-tax dollars through a Section 125 cafeteria plan. In retirement, you're typically paying the full premium with no subsidy. You can verify by requesting a benefits statement from your former employer or the plan administrator. They should be able to confirm that your payments are being made with after-tax dollars. The statement from them would also serve as excellent documentation for your tax records in case of an audit.

This! Standard deduction for 2024 is $14,600 for single filers and $29,200 for married filing jointly. Make sure itemizing actually benefits you before going through all this documentation hassle.

That's a really good point about the receipts! Do you think using a translation app on my phone for each receipt would be sufficient, or should I get professional translations if I get audited? Also, what's the best way to document my existing equipment? Would photos with serial numbers be enough?

A translation app is usually sufficient for basic receipt documentation as long as you do it at the time of purchase and keep both versions. If you do get audited, then you might need professional translations for any significant expenses, but that's a bridge to cross only if necessary. For documenting equipment, photos with visible serial numbers are good, but I recommend going a step further. Create a spreadsheet listing all equipment with purchase dates, prices, serial numbers, and current value. Take photos/video of everything together before your trip. Some of my clients even get a dated letter from their insurance company listing covered photography equipment, which serves as third-party verification of prior ownership.

I used TurboTax Self-Employed last year for my graphic design business which included some travel. It asks basic questions about business travel but doesn't really give you the detailed guidance you need for international business trips. It won't tell you about the 75% rule or help with documentation requirements. If you have a complex situation like international business travel, I'd recommend at least consulting with a tax pro who specializes in creative businesses.

19 What payroll system did you end up using that handled ITINs well? We're using an older version of QuickBooks and I'm worried it might have the same issue.

4 We switched to Gusto and it's been handling ITINs without any problems. Most of the newer cloud-based payroll systems seem equipped for this now. QuickBooks Online also works with ITINs from what I've heard, but the older desktop versions might give you trouble. Before you switch systems though, you might want to contact QuickBooks support about your specific version - some of them can be updated or have workarounds. The key thing is making sure the system doesn't automatically reject numbers starting with 9 during validation checks.

10 How do you determine if an ITIN holder is exempt from FICA? Is there some documentation they need to provide?