Don't overlook your bank! Chase, Bank of America, and Wells Fargo all offer payroll services for small businesses that are surprisingly affordable if you're already a business customer. Worth checking what yours offers.

Just wanted to add another perspective here - we went with Gusto Simple for our 2-person setup and it's been solid. Yes, it's a bit more than some options at $40/month + $6 per employee, but the peace of mind is worth it. What really sold me was their customer support. When we had questions about setting up our S-Corp payroll correctly (since we're owners paying ourselves), they actually helped walk us through the reasonable compensation requirements and made sure we were structured properly from day one. The automatic tax filing has been flawless for over a year now, and the year-end W-2 generation was seamless. Sometimes paying a little extra upfront saves you from much bigger headaches down the road with compliance issues.

22 Has anyone used TurboTax to report their portion of losses from a JTWROS account? Is there a specific section for this? I'm in a similar situation with a joint account with my sister, and we had about $5,800 in losses last year.

I went through this exact situation two years ago with my business partners. We had a JTWROS account that generated about $4,500 in capital losses, and I was completely confused about how to handle it on our tax returns. What I learned is that you absolutely can split the losses proportionally among the actual owners, but documentation is key. Since Jake's SSN is on the 1099-B, he'll need to report the full $7,000 initially on his Schedule D. However, each of you should also report your $2,333 portion on your individual returns. The critical part is including a statement with each return explaining the joint ownership arrangement. I used language like: "This capital loss represents my 1/3 ownership share of losses from jointly-owned brokerage account [account number], with total losses of $7,000 reported under SSN [Jake's SSN]." Make sure you all keep records of your equal contributions to the account - bank statements, transfer records, etc. The IRS wants to see that your claimed ownership percentages match reality. Also, consider drafting a simple written agreement between the three of you documenting the equal ownership split, even if it's after the fact. One tip: file your returns around the same time so if the IRS has questions, they can easily see all three related returns and how the total adds up correctly.

One strategic tax planning tip related to capital losses: if you anticipate having substantial capital gains in the near future, you might want to consider NOT claiming the full $3,000 deduction against ordinary income in some years. While this sounds counterintuitive, if you're in a relatively low tax bracket now but expect to be in a much higher bracket when you realize those future gains, it might be more tax-efficient to preserve more of your carried-over losses to offset those future gains. For example, if you're currently in the 12% bracket but expect to have gains that would be taxed at 20% plus the 3.8% NIIT in the future, saving those losses could give you a better overall tax benefit.

This is such a helpful thread! I'm in a very similar situation - had about $22k in crypto losses from 2020-2021 and I'm finally seeing some recovery in my portfolio this year. One thing I want to emphasize for anyone reading this: definitely keep meticulous records of everything. I learned this lesson when I tried to reconstruct my loss carryover amounts last year and had to dig through old exchange records, some of which were from platforms that no longer existed! Also, a practical tip - if you're using tax software, double-check that it's correctly carrying forward your losses year to year. I caught an error in TurboTax where it somehow "lost" about $3k of my carryover between 2022 and 2023. Had to manually correct it. The peace of mind knowing these losses can eventually offset future gains makes the whole painful experience a bit more bearable. Thanks to everyone who shared their experiences - really valuable information here!

This situation sounds incredibly stressful, and I really feel for you having to navigate these banking hurdles while managing medical treatments! After reading through all the excellent advice shared here, I wanted to add one more potential solution that worked for a friend of mine in a similar situation. Have you considered asking your bank about their "banker by appointment" or "personal banker" services? Many banks offer after-hours appointments for established customers, especially for significant transactions like this. Even if your regular branch doesn't advertise this service, the regional or main branch might have a banker who can meet with you both outside normal hours. Also, if your husband has any banking relationships through his employer (like direct deposit), that bank might have more flexible policies or be willing to work with you as a potential new customer. Some employers also have HR departments that can help employees navigate financial logistics - it might be worth him asking if they have any banking partnerships or resources. The key really seems to be persistence and finding the right person with decision-making authority. Your medical circumstances combined with your husband's work constraints absolutely warrant accommodation. Don't let them brush you off with "that's just our policy" - keep asking to speak with supervisors until you find someone who can help. Keep us updated on your progress! This thread has become such a valuable resource for others facing similar challenges.

Reading through all these excellent suggestions, I'm hopeful you'll find a solution! One additional approach that might help: some banks have "exception approval committees" that meet weekly to review unusual circumstances. If the front-line staff and branch managers can't help, ask specifically if your situation can be submitted to their exception committee for review. Frame it as a request for reasonable accommodation due to medical circumstances and work schedule conflicts. Also, consider timing your calls strategically. I've found that calling banks mid-morning (around 10am) often connects you with more experienced staff who have greater authority to make decisions. Avoid calling first thing in the morning or right before closing when you're more likely to get rushed responses. If all else fails and you do need to use a check cashing service temporarily, try calling local grocery stores with customer service desks. Some offer check cashing with lower fees than dedicated check cashing businesses, especially for tax refund checks. Just make sure they can handle the amount - many have lower limits than what you need. The combination of your medical treatments and your husband's work schedule creating this timing conflict is exactly the type of situation banks' accommodation policies are designed to address. Stay persistent and keep escalating until you find someone with the authority to help!

One strategy I've used to manage AMT with ISOs is exercising small batches strategically throughout the year rather than doing them all at once. This helps avoid crossing into higher AMT brackets. Also, don't forget about the 83(b) election for early exercise if your company allows it! If you can exercise when the spread between strike price and FMV is small or zero, you can potentially avoid AMT altogether.

Great point about the 83(b) election, Dylan! That's definitely a strategy more people should know about. For OP's current situation though, since they've already exercised, the key decision is really about timing the sale. One thing I haven't seen mentioned yet is the wash sale rules. If you're planning to sell and potentially buy back in later, make sure you wait at least 31 days before repurchasing to avoid having the loss disallowed if the stock drops. Also, given your numbers ($33/share spread on 1,500 shares = $49,500 AMT adjustment), you're definitely in territory where professional tax advice would pay for itself. The AMT exemption phases out at higher income levels, so depending on your other income, you might be hit harder than you think. If you absolutely need the cash now, selling early might be the right move to avoid the AMT uncertainty. The difference between ordinary income rates and long-term capital gains probably won't be as painful as getting stuck with a big AMT bill you can't immediately use the credit for.