Something to remember about the dependent care FSA: if you and your spouse both have access to one through work, the $5000 limit is per family, not per person. Made that mistake one year and had to deal with excess contributions on our tax return. Not fun!

For the healthcare side, remember that FSA and HSA are completely different things! FSA = Flexible Spending Account, use-it-or-lose-it each year HSA = Health Savings Account, yours forever, rolls over yearly You mentioned both in your title but then only talked about FSAs. If you actually have access to an HSA (requires being on a high-deductible health plan), that's usually a better long-term financial choice than an FSA because you never lose the money and can invest it for retirement.

One thing nobody's mentioned - double check with your girlfriend if she can get insurance through her own employer. Often it's cheaper overall (even if her employer's plan is more expensive than her portion of yours) because of this imputed income tax situation. In my case, my partner and I were paying about $180 extra per month for her portion of my plan, but the imputed income was valued at $450/month, putting me in a higher tax bracket and costing us way more in the end. She switched to her company's plan at $240/month, and we still saved money overall!

This is such a common surprise for people! I went through the exact same thing when I added my boyfriend to my insurance plan last year. The imputed income concept is confusing at first, but once you understand it, you can plan better. One thing that helped me was setting up a separate savings account specifically for the extra taxes from imputed income. I calculated roughly how much extra I'd owe (about 25% of the monthly imputed income value in my tax bracket) and automatically transfer that amount each month. This way I'm not scrambling to find the money at tax time. Also, make sure you're keeping good records of what your girlfriend reimburses you. While it doesn't change the tax situation, having clear documentation of these payments can be helpful if you ever get questions about your finances. Some people even set up a simple written agreement just to keep everything transparent. The silver lining is that you caught this relatively early in the year, so you have time to adjust your withholding or quarterly payments if needed!

One more thing to consider - timing! If you're thinking about switching from SEP IRA to Solo 401k, remember that Solo 401k plans must be established by December 31st to make contributions for that tax year (though you can actually fund it until your tax filing deadline). SEP IRAs can be set up and funded all the way until your tax filing deadline (including extensions) for the previous year. This flexibility is one advantage SEPs have over Solo 401ks.

Just wanted to add my experience as someone who made this exact transition last year. I was in a similar situation with an S-corp - low W-2 salary relative to business profit, and hitting the SEP IRA contribution ceiling way too early. After talking to my CPA, we decided to gradually increase my W-2 salary over two years while transitioning to a Solo 401k. The key was finding the sweet spot where the additional payroll taxes from higher salary were offset by the tax benefits of larger retirement contributions. For 2024, I increased my salary to $35K (from $18K) and switched to a Solo 401k. Even with the extra payroll taxes, I was able to contribute about $15K more to retirement than I could with the SEP IRA at my old salary level. The math worked out to significant long-term savings. One tip: if you do switch to Solo 401k, make sure your plan document allows for both employee AND employer contributions. Some providers default to employee-only contributions, which would limit your total contribution potential.

Be careful with income on line 11 - sometimes it can have foreign tax withholding associated with it that you can claim as a credit. My partnership K-1 had foreign interest income on line 11 last year and I almost missed claiming the foreign tax credit. Check if there's anything on line 16 about foreign taxes paid!

Great question! In addition to the excellent answers already provided, I'd like to mention a few more types of income that can show up on line 11: - Income from Real Estate Investment Trust (REIT) distributions that don't qualify as dividends - Gain/loss from mark-to-market elections on securities - Income from commodity futures contracts held as investments - Certain foreign currency gains/losses from investment activities - Income from credit default swaps and other derivative instruments One important tip: if you have significant amounts on line 11, especially from complex financial instruments, consider keeping detailed records of the source documents. The IRS may ask for additional information during an audit since this line often contains less common types of investment income. Also, don't forget to check if any of this income has associated expenses that might be deductible - sometimes partnerships will report the gross income on line 11 and related investment expenses elsewhere on the K-1.

Anyone know how far back the IRS keeps 1099 records? I'm missing some from 2020 and wonder if it's even possible to get them now.

Just went through this exact situation last year when I lost my 1099s from freelance work! The advice about contacting the companies first is spot on - that's definitely your fastest option. One thing I'd add is that your brother should also check if any of the companies that paid him used payment platforms like PayPal, Stripe, or Square. These platforms often have year-end tax documents available in your account dashboard that you can download as PDFs. I was able to get 3 out of 5 missing forms this way. Also, if he's really stressed about the deadline, filing for an extension buys him time to get everything sorted properly. Better to file accurately late than to rush and make mistakes that could trigger an audit later. The penalty for late filing is usually much less scary than people think, especially if he ends up owing little or getting a refund. Hope this helps ease some of his anxiety - it's really not as catastrophic as it feels in the moment!