For most software engineers it's not hard to build up a significant emergency fund. I'd advocate for 6 figures. Feel free to invest 80% of that as well in something liquid. Keep at least 3 months in cash.
I would go with CIT Savings Connect, they have historically been near the top and they have a nice website.
https://www.doctorofcredit.com/high-interest-savings-to-get/
So pay for all your healthcare expenses with non HSA funds, keep track of the expenses, and eventually, you probably will have accumulated $10k or $20k of healthcare expenses you can reimburse yourself for IF you exhaust your regular emergency fund.
Adverse selection means an individual can’t get the same insurance a big organization buying for a large group can; ACA exchanges may (state markets vary a lot) mitigate that somewhat, but they don't fully make up for it. Part of this is orice for benefits, but the same benefit packages may not be available to you at any price (adverse selection means creates a kind of feedback loop where for certain things, there is no price where offering an option isn't a losing deal for the offeror, because the only people who would take it would be the ones for whom it would be a net loss for the seller to provide it.)
COBRA, though, allows you to keep your bigco insurance when you lose your job, as long as you take over both sides of the payment, for up to 18 months. So, in that sense, it is about the money.
The problem for programmers is not cost of insurance, the problem is weird long-tail shit like insurance denying treatments you need, or wildly over-billing you.
Its value is not what it pays for, it's value is capping out-of-pocket maximums in the worst-case. (Any serious medical situation will quickly run you up to them.)
Also, have you ever looked at the 'Employer pays' line item on the insurance section of a bigco paystub? Mine is more than my rent. (Maybe I should move to a bigger apartment.)
I understand that there's a huge sticker shock to having to pay your + an employer's portion of insurance, but it's still a function of money, and working for a bigco that does 7% layoffs every 8 years is a really good way to earn a lot of money.
And it's not like there are any 'play it safe' places in a recession. You can't predict the future, and small companies go belly-up, and do layoffs just as much as big ones.
That $2400/mo is the true cost of insurance. Your bigco employer pays most of it, and you pay the rest.
So, yes, when that part of your pay is lost, it sucks. It sucks a lot. But that's not what we're discussing. We're discussing the financial situation you're in when you get paid bigco wages, and have to deal with 8% layoffs every 8 years, or working somewhere else, where you get paid substantially less (And also probably have to deal with layoffs, it's just that they don't hit the front page of HN).
It's a financial no-brainer to me. If the wage delta is more than a rounding error, I'm much better off, financially in just taking the money.
Point being it's still just money at the end, and saving up for a rainy day fund should also include COBRA payments in the calculation of how long the fund will last.
But yes, family plans are expensive (I've seen them average about $1500 a month for COBRA family plans), but that just gets to the point about saving enough in a rainy day fund to include healthcare costs.