HDHP for you most likely. You can incur $824 in healthcare costs/year before PPO could possibly cheaper. That'll easily cover a couple doctor's appointments. 1 true annual check is free even on the HDHP.

It's not a slam dunk the first year or two but you will likely see faster income growth. You of course are giving up some stability and the pension.

If work from home is that important to you, I think it's fine making the jump. Some orgs just don't get it and are willing to lose good talent.

You have a crappy HDHP plan. Many have drastically lower deductibles. So it doesn't make sense in your case.

The earliest he can get insurance coverage is Jan 1st. Unless something wasn't mentioned, he has no QLE for enrollment now.

He's pretty screwed TBH. Sorry, just don't want to sugar coat it.

Medicaid is unlikely as you said.

No insurance plan is going to allow enrollment right now except a new employer plan. Marketplace open enrollment starts in November for coverage to take effect Jan 2023.

He needs to talk to the financial aid people at the hospital ASAP. It can be tricky to get surgery even scheduled without prepaying or insurance.

You're vulnerable to identity theft regardless of whether you have any active credit cards.

> taxes may be a whole new level of crazy with the way society is going.

They've been going down for at least 20 years.

I think you're in pretty good shape. Have you gotten a social security estimate at www.ssa.gov? That alone could cover a good portion of your retirement expenses.

You mentioned cutting your retirement savings in half. So from 45K to 22500. With 500K now, adding 22500/year, in 10 years you'll be at 1.3 million. Maybe less as you shift to a less aggressive portfolio.

Is your house set to be paid off when you retire? The mortgage was included in your expenses based on how I read your post.

If the vacation club is a time share, stay the hell away.

> I'm 100% remote and I plan to take my laptop with me most of the time.

I really recommend not doing this. I do this as well sometimes for quick weekend trips, but I don't consider these vacations. I may fly in late Thursday, work Friday, then have the weekend. But if I'm going to Hawaii for a week or two, I'm not even bringing my laptop.

Ah that's a small cost differential. I usually see much higher differences in premiums alone so the HDHP almost always make more sense.

I think you could have COBRA and your new employer's coverage for 2022 but it wouldn't make any financial sense if you've already met your OOP max.

Based on your numbers, I think COBRA makes sense.

However, make sure you enroll in 2023 coverage from your new employer during their open enrollment. From some quick googling, it's suggested that dropping COBRA coverage willingly (not exhausting it) will not be a qualifying event to enroll outside of open enrollment.

> but I'm scared to enroll in high deductible plan (requirement to enroll in HSA) because for a typical primary care visit, for FSA, I only pay $20 Copay, but with high deductible plan, I need to pay 20% coinsurance. Thanks in advance for the info.

But you're probably paying more each paycheck for that copay plan. So you have to compare total costs.

If the copay plan costs $200/month, but the HDHP costs $100/month, you definitely come out ahead on the HDHP for the first $1200/year in medical costs.

What's the premium difference? I've rarely seen a family plan where the HDHP was worse than traditional PPO plan because the trad plan was like $1000/month and the HDHP was $500.

FSA/HSA cards are the most hassle free way, although you may still be required to produce a receipt in some circumstances.

FSA is use it or lose it, so there's a risk of losing money if you don't incur enough expenses.

Even with an FSA, it's technically better to use your own credit card for rewards, then reimburse yourself.