Has anyone actually calculated the total difference between employer pretax health insurance vs marketplace plans when considering ALL factors? I'm in similar situation but also wondering about: 1. Quality of network (my employer plan sucks) 2. Premium differences 3. Tax implications 4. Out-of-pocket differences My employer takes $515/month pretax but the deductible is $7000! Marketplace plan is $560/month but deductible only $3500. Trying to figure out total cost including taxes.

One thing to consider that hasn't been mentioned yet is whether your employer offers a Health Savings Account (HSA) option with their high-deductible health plan. If they do, that's another significant tax advantage you'd lose by going to marketplace coverage. HSA contributions are triple tax-advantaged: deductible going in, grow tax-free, and withdrawals for qualified medical expenses are tax-free. For 2025, you can contribute up to $4,300 for individual coverage or $8,550 for family coverage. This could potentially offset some of the higher deductible concerns while maximizing your tax benefits. Also worth checking if your employer contributes anything to an HSA on your behalf - that's essentially free money you'd be giving up. Some employers contribute $500-2000 annually to employee HSAs, which changes the math considerably when comparing total compensation packages. If HSA isn't available with your current plan, that might actually strengthen the case for switching to marketplace coverage, especially if you can find an HSA-eligible high-deductible plan there.

Does anyone know if this same approach works for other types of income? My 14yo son has a small YouTube channel that just started generating ad revenue, but they required my info since he's underage.

This is really helpful information! I had no idea there were specific exemptions for different types of work that minors do. My 17-year-old works as a camp counselor during summers and also does some pet-sitting through a neighborhood app. I'm wondering if there are other exemptions I should know about beyond the domestic service one that was mentioned for babysitting. It sounds like the type of work might make a difference in whether self-employment taxes apply or not. Does anyone know where I can find a comprehensive list of these exemptions for minors? Also, the Roth IRA idea is brilliant - I never thought about starting retirement savings this early but the compound growth potential is amazing. Definitely going to look into setting that up for my daughter once we get her tax situation sorted out.

I completely understand your anxiety about this - the "jeopardy" language is definitely designed to get your attention! Here's what I'd recommend based on your situation: **Don't wait** - even though you're only waiting for one W2, that lien/levy notice means the IRS is ready to take action. A few key points: 1. **Call the IRS immediately** at the number on your notice. Explain you're waiting for a missing W2 and plan to file soon. They can often put a temporary hold (60-90 days) on collection actions. 2. **Request your wage transcript** from IRS.gov while you wait - this shows all reported W2 info and might have enough detail to file without the physical W2. 3. **Set up a minimal payment plan** if you can't reach them by phone. Even $25/month stops collection and shows good faith. Online setup is only $31 vs $107 by phone. The key thing is **communication** - the IRS doesn't know you plan to pay with your refund. From their perspective, you're just ignoring a debt. Once you make contact and explain your situation, they're usually reasonable about working with you. Don't risk a lien on your credit report over $650 - it's not worth the long-term damage for a relatively small amount. Take action today!

I had almost this exact same situation last year - owed about $700 and got that scary "jeopardy" notice while waiting for a delayed 1099 from a freelance gig. The language in those notices is definitely designed to get you moving fast! Here's what worked for me: I called the IRS number on the notice (took about 2 hours on hold, but I got through). The agent was actually really understanding when I explained I was just waiting for tax documents. She put a 90-day collection hold on my account, which gave me plenty of time to get everything sorted out. The key thing they told me is that once you receive that "lien/levy warning," you're basically at the final stage before they take action. They don't know you're planning to use your refund to pay it off - from their system, it just looks like you're ignoring the debt. Don't stress too much about the $650 amount, but definitely don't ignore the timeline. Even setting up a $25/month payment plan online would stop the collection process immediately if you can't get through by phone. You can always pay it off in full once you file and get your refund. The worst thing you can do is nothing - I've seen people end up with liens over tiny amounts just because they thought it wasn't worth dealing with. Take care of it this week!

I went through this exact same process about 6 months ago and can confirm what others have said - the sequence is crucial. I made the mistake of overthinking it initially and got stuck in analysis paralysis. Here's what I learned from my experience: 1. The IRS EIN application system is designed around legal entity types, not tax elections. So when you see "LLC" vs "S Corporation" options, they're asking about your legal structure, not your tax treatment. 2. Apply for your EIN using "Limited Liability Company" and your full legal name including "LLC". Don't try to work around the system by omitting "LLC" or using a DBA - this could create complications later. 3. The online EIN application really does give you the number immediately in most cases. I was surprised by how fast it was. 4. File Form 2553 as soon as you get your EIN. Don't wait - the 2 month 15 day deadline is firm, and while there's late election relief available, it's better to just file on time. One thing I wish I'd known: make sure your LLC Operating Agreement doesn't have any provisions that would disqualify you from S Corp treatment (like disproportionate distributions or more than 100 members). It's worth reviewing this before you file the election. The whole process took me less than a week once I understood the proper sequence. Good luck with your application!

I just went through this exact process last month and wanted to share what worked for me since I see a lot of great advice here but also some confusion in the comments. The key insight that finally clicked for me: the EIN application asks about your LEGAL entity structure, while Form 2553 is about your TAX election. These are completely separate things, which is why the IRS website seems confusing when you're trying to do both at once. Here's exactly what I did: 1. Applied online for EIN selecting "Limited Liability Company" - used our full legal name including "LLC" 2. Got the EIN instantly (literally took 10 minutes total) 3. Downloaded Form 2553 from IRS website 4. Had both LLC members sign it 5. Mailed it certified mail the next day One thing I'll add to what others have said: make sure you understand the "reasonable compensation" requirements once your S Corp election is effective. As an S Corp, you'll need to pay yourself a reasonable salary (subject to payroll taxes) before taking distributions. This is something to budget for since it affects your cash flow. The whole thing was much simpler than I expected once I stopped overthinking it. The IRS systems actually work pretty well when you follow the proper sequence!

Just wanted to add something important that hasn't been mentioned yet - make sure you keep detailed records of the original loan transaction too. Since you withdrew $50K in cash from your bank, that withdrawal should be documented on your bank statements. This creates a clear paper trail showing the money left your account and then returned, which helps establish the legitimacy of the loan arrangement. Also, regarding the 15% interest rate you charged - that's actually quite reasonable and well above the current Applicable Federal Rates (AFR), so you shouldn't have any issues with the IRS questioning whether this was a legitimate loan versus a disguised gift. The AFR for short-term loans is currently much lower, so your 15% rate clearly shows this was a commercial-style transaction. One more thing to consider: if you plan to make similar loans in the future, you might want to consider having your friend write you a check for the interest portion instead of paying in cash. This creates better documentation and avoids the complications others mentioned about carrying large amounts of cash.

I've been through a similar situation with personal loans to family members, and I learned the hard way that documentation is everything. Here's what I wish I had known from the start: First, yes, you absolutely need to report that $7.5K as interest income on your tax return. Even though it's cash sitting in your safe, it's still taxable income the moment your friend paid it to you. The IRS doesn't care about the physical form - income is income. Second, while your loan agreement is a good start, I'd strongly recommend creating a supplemental memo now documenting the complete transaction timeline. Include the withdrawal date from your bank, the loan disbursement date, the repayment date, and amounts. Even though this is after-the-fact documentation, it shows you're treating this as a legitimate business transaction. Third, consider depositing that $7.5K interest into your bank account rather than keeping it as cash. This creates a clear audit trail and removes any potential complications from having large amounts of undocumented cash. Plus, if you ever get audited, having bank records showing the interest income makes everything much cleaner. Finally, make sure your friend understands this was a legitimate loan with interest, not a gift. If the IRS ever questions either of you about it, you both need to tell the same story about this being an arm's length transaction.