Thanks for bringing up the non-tax factors! You're right that I should be looking at the whole picture. The deductible on my private plan is actually $3,500 lower than my employer's plan, and my regular specialists are all in-network with my current coverage. I don't qualify for ACA subsidies unfortunately - my income is too high. But the network difference is definitely significant. I guess I need to assign some dollar value to having better coverage and a lower deductible to make a fair comparison.

Absolutely! A $3,500 deductible difference is significant. One approach is to consider your typical annual healthcare usage. If you regularly meet your deductible, that $3,500 is a real savings that offsets some of the tax benefits. Also consider coverage for specific services you use regularly. For example, I discovered my employer plan had much worse mental health coverage than my private plan - fewer visits covered and higher copays. For someone who uses therapy regularly, that difference alone could be worth thousands.

This is an important distinction! The OP mentioned they're employed "by contract" but that could mean either W-2 through a contracting agency or true 1099 self-employment. If you're W-2, you can't deduct private health insurance premiums against self-employment taxes since you don't pay those - your employer pays half of FICA and you pay half through withholding. But if you're 1099, the self-employed health insurance deduction is super valuable. It reduces your income for income tax purposes AND self-employment tax purposes, which is huge.

That's a really good point I hadn't considered. Do you think it would help if I framed it as an option the company could offer to everyone rather than just for my situation? Maybe present research on how many employees might have student loans?

Approaching it as a company-wide benefit is definitely the better strategy. Do some research on companies in your industry that offer this benefit and how they implement it. Gather data on average student loan debt for professionals in your field and typical program structures. Then create a brief proposal showing the potential impact on employee retention and recruitment. Many companies find that student loan assistance programs significantly improve their ability to attract and retain younger talent, which often provides ROI that exceeds the program costs. Frame it as a competitive advantage rather than a personal accommodation.

The matching approach is smart. My company started with $50/month matching and it was popular enough that they increased it to $200/month the following year. Much easier for them to implement than lump sums.

You might be onto something! I just checked our records and we paid approximately $26,200 in state taxes this year. That's pretty close to the $24,500 discrepancy I was seeing. How exactly should I handle this on the forms to make them reconcile properly?

You'll need to add the state tax amount back on your M1 form in the section for additions. Most state forms have a specific line for "Taxes paid to other states" or "State, local, and foreign income taxes." This addition reconciles the difference between your federal taxable income and state taxable income. Make sure you're only adding back income taxes though - other taxes like property tax or payroll taxes are generally deductible on both returns. Once you add this adjustment, your reconciliation between Schedule K line 18 and M1 line 8 should be much closer, if not exact.

Yes! This is super important. The $850k distribution OP mentioned won't show on the M1, but it MUST be tracked for each shareholder's basis. If their basis goes below zero because of distributions, they could end up with unexpected capital gains. I recommend keeping a basis worksheet for each shareholder from year to year.

Do you have any suggestions for a template or example of a simple agreement that worked? I'm not sure what should be included besides the basics.

A basic promissory note doesn't need to be complicated. Include the names of both parties, the loan amount, when and how payments will be made, and any consequences for late payments. Even if you don't plan to enforce it strictly, having it written down prevents misunderstandings. You should also consider including what happens if you lose your job or have an emergency - would they allow you to pause payments? Will the term be extended? Better to discuss these scenarios upfront when everyone's happy. I found some free templates online that worked great - just search for "family loan agreement template" and customize one to your situation.

Did you have any issues with taxes or the IRS because of the no-interest part? Did either of you have to report anything on your tax returns?

Did you have any issues with either employer finding out about the other job? I'm thinking about doing this but worried my main job might consider it a conflict of interest or something.

I didn't have any direct issues because the jobs were in completely different industries (office admin work during weekdays and retail on evenings/weekends). Neither company had policies against outside employment. However, I did almost get caught once when I had to call out sick from my weekend job and my manager there tried to reach me during a weekday meeting at my main job. I'd definitely recommend checking your employment contracts first. Some companies do have clauses about outside employment, especially if it could be considered a conflict of interest or if they think it might affect your performance.

I tried using that IRS calculator thing and got super confused. It asked for way more information than I had available. Is there a simpler way to figure this out?