About the 40k bills, I would suggest not paying them immediately and talking to your insurance company regularly (yes, it's exhausting and a PITA). Because of their slower systems, they're probably doing billing calculations on a monthly cycle so if you got multiple bills within a time period, their systems haven't realized that you've hit your out of pocket max (in engineering terms you've got multiple concurrent processes running, but they're all using a cached version of your total billed). Also most billing departments take 60-90 days to bill you so your providers are optimized for billing quickly.
Also, if you call in about your bill you can usually get discounts for paying promptly or at least get put on a payment plan.
Yeah, we're pushing back on it, and I'm dead lucky to not only have an employer, but one that's provided some legal assistance so far.
If anyone wants to turn this thread back around to "what can tech companies do", it's extending legal and financial services to employees who have their backs to the wall in situations like this.
I liked my manager before this, a lot, but I'd take a barrage of bullets for her now.
Actually for anyone who finds themselves in a situation like this: https://www.reddit.com/r/personalfinance/comments/b01179/som... has some great advice.
And if you work for a tech company, many are able to really help you (since most tech companies skew young and healthy, ie low-risk, they are able to really push on the insurance companies). I know of at least one case at AppNexus a few years ago
Also, if you call in about your bill you can usually get discounts for paying promptly or at least get put on a payment plan.