Is this approach actually legal? I thought if you offer a retirement plan it has to be available to all eligible employees. Wouldn't having separate plans violate some non-discrimination rules?

This is a common misconception. The key is in how you structure the business entities. If the owners operate through a separate entity (like a partnership) from the employee-hiring entity, then you can legally establish different plans. You'd need to consult with a tax professional to ensure your specific business structure qualifies, but many small businesses with similar structures to yours successfully implement this dual approach. The critical factor is having proper documentation of the separate business entities and ensuring you follow all IRS guidelines for each plan type.

That sounds perfect! $49/month is much more reasonable. Does Guideline handle all the compliance testing and Form 5500 filing? Also, could you explain a bit more about how the discretionary profit sharing worked in your case?

Yes! This happened to me too with PBGC forms. The IRS computer systems automatically flag accounts when they receive certain forms, even if you don't claim the associated credits.

That's really good to know - my bankruptcy was discharged about 14 months ago, so sounds like I should be past that waiting period. I do have one tax return I haven't filed yet because I knew I'd owe and couldn't pay. Should I get that filed ASAP before contacting them about the Fresh Start options?

Yes, absolutely file that outstanding return immediately. The IRS won't even discuss resolution options until you're in compliance with all filing requirements. Even if you can't pay what you owe, getting the return filed is the necessary first step. Think of it this way - the IRS sees unfiled returns as someone trying to hide or avoid their obligations entirely, while someone who files but can't pay is at least being transparent about their situation. Once you've filed everything, then you can approach them about payment options through the Fresh Start program with a much better chance of success.

I think this depends on your specific situation though. The IRS doesn't actually expect you to create more debt (like maxing out credit cards) to pay tax debt. They look at reasonable collection potential. When I submitted my OIC, I just had to document my current financial situation honestly.

Thanks for the tip about entering them separately! Do you know if TurboTax will automatically ask me about the medical insurance exception, or do I need to look for that specifically somewhere?

TurboTax should ask you about exceptions after you enter each 1099-R form. When it asks about the distribution code (Box 7), it will then follow up with questions about your situation. If you indicate you were unemployed, it should specifically ask if you used any of the money for health insurance premiums. If it doesn't automatically prompt you, look for a section called "Exceptions to Tax Penalties" or something similar after entering your 1099-R information. Make sure you have documentation of your insurance premium payments during your unemployment period, as you'll need this if you're audited.

I used it last year for a similar retirement withdrawal situation. The expert was helpful in confirming I qualified for an exception to the penalty since I was using the money for health insurance during unemployment. For complex situations like multiple 1099-Rs with no W-2s, I'd say it's worth the extra cost for the peace of mind.

Thank you! My income is around $48,000 - would I still qualify for EITC? And my brother is still in high school, but I am paying for some tutoring services. Would those count as educational expenses?

With $48,000 income and two dependents, you should still qualify for some EITC, though not the maximum amount. The phase-out for Head of Household with two qualifying dependents starts higher than your income, but you'll get a partial credit. Every bit helps! For educational expenses, unfortunately tutoring for high school generally doesn't qualify for the education credits. Those are primarily for post-secondary education (college, vocational schools, etc.). However, if the tutoring is related to a medical condition and prescribed by a doctor, you might be able to count it as a medical expense instead.

This is super important! And just adding on - there's sometimes a gap between disability approval and Medicare coverage starting. During that time, look into if your state has a Medicare Savings Program that could help with premiums.