That's a great suggestion about the IRA! I never thought about that. If I'm gonna hit the contribution limit issue again next year, maybe I should reduce my 401k and put some in an IRA instead? Would a backdoor Roth make sense in this situation? I've heard about that but don't really understand how it works.

Exactly - if you know you'll likely face this issue again, you could contribute just enough to your 401(k) to stay under whatever threshold your plan administrator suggests, then put the rest in an IRA. Regarding backdoor Roth - that's mainly useful if your income exceeds the limits for direct Roth IRA contributions. You'd contribute to a traditional IRA (no deduction) and then convert it to Roth shortly after. It's a perfectly legal workaround for the income limitations, but has some nuances if you have existing traditional IRA balances (pro-rata rule). Would definitely be worth considering if you're over the Roth income limits.

Wait really? I thought it would count for the tax year when the original contribution was made. This is getting confusing...

It's the combined total of all your foreign financial accounts at any point during the year. So if the aggregate (combined) maximum value of all your foreign accounts exceeded $10,000 at any time during the calendar year, you need to file an FBAR - even if no single account ever exceeded $10,000. For example, if you have three foreign accounts with maximum balances of $4,000, $3,000, and $4,000 during the year, your aggregate maximum would be $11,000, triggering the FBAR filing requirement. The key is to look at when all accounts were at their highest, even if that happened on different days.

Thank you for clarifying! I definitely need to file then. I've had 5 accounts in my home country for years and never filed because each one stays small, but together they're definitely over $10K. Better late than never I guess?

That's actually super helpful advice! I wouldn't have thought to document everything like that. Will definitely save all confirmation emails and screenshots when I submit. Did you mail your FBAR or file electronically? I'm assuming electronic is better for creating that paper trail?

Definitely file electronically - it's the only option now anyway. The FinCEN BSA e-filing system will give you a confirmation receipt with a BSA Identifier number immediately after submission. Save that PDF confirmation right away and also take screenshots of the successful submission page. Electronic filing creates a much better trail than paper ever did, plus it processes much faster. Just make absolutely sure all your information is accurate before submitting, especially account numbers. Simple mistakes can cause headaches later.

Thanks for bringing up FSA/HSA options - I do have an HSA but haven't been maxing it out. Does anyone know if wheelchair van modifications would qualify for HSA funds? And would this approach be better than trying to claim them as itemized deductions?

Yes, the van modifications would generally qualify for HSA funds since they're considered medical expenses. The advantage of using HSA funds is that you get the tax benefit regardless of whether you itemize deductions or not, and you don't have to meet that 7.5% of AGI threshold that applies to itemized medical deductions. If you have the option, using HSA funds is almost always more advantageous than claiming itemized deductions for the same expenses. The HSA gives you triple tax benefits: tax-free contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.

Totally agree about detailed invoices! We did something similar for my mom, and the modification company just gave us one lump sum initially. We had to go back and ask for an itemized breakdown of every component. Made a huge difference when filing.

That's a great point! Our modification company was pretty good about providing details, but I still had to ask for clarification on a few items. The more specific the better - like having separate line items for the ramp mechanism, the door widening, the specialized restraint system, etc. Our accountant even suggested taking photos of all the modifications as additional documentation.

If I'm both partners in an LLC (single-member LLC), do I still need to file a 1065? I thought in that case it just goes on my Schedule C?

You're mixing up two different business types. A single-member LLC is treated as a disregarded entity by default and would file Schedule C with your personal return, not Form 1065. A partnership requires at least two partners. If you're the only owner, you don't have a partnership by definition. Single-member LLCs report on Schedule C unless they've elected to be taxed as a corporation. Multi-member LLCs are treated as partnerships by default and file Form 1065 along with Schedule K-1s for each partner.

Is there a minimum amount you need to make before you have to do the quarterly payments? My side business only makes like $3k a year.

Generally, you need to make quarterly estimated tax payments if you expect to owe at least $1,000 in taxes for the year. However, you can avoid penalties if you pay at least 90% of the tax for the current year or 100% of the tax shown on your previous year's return (whichever is smaller). For a small side business making around $3k, it might not trigger the requirement depending on your tax situation, but it's always good to calculate your expected tax liability to be sure. Self-employment tax (15.3%) kicks in when you have $400 or more in net earnings, so even small businesses can sometimes create tax obligations.

That's an interesting point - I'll have to double check the paperwork. The financing company definitely framed it as a way to exercise without selling any shares (that was their main selling point), but now I'm wondering if there were any partial sales happening behind the scenes to cover taxes.

Definitely check the paperwork carefully. Some financing companies structure the transaction as a loan against the shares rather than a true cashless exercise, which preserves the tax treatment of a regular exercise-and-hold strategy. The key documents to look for would be any statements showing exactly how many shares you received versus how many you purchased, and confirmation of exactly what taxes were paid at the time. If they paid estimated taxes rather than withholding, that might explain part of the confusion too.

83(b) elections are for restricted stock, not ISOs. They don't apply in this situation at all. ISOs are governed by different tax rules.