Also, my password manager is a critical part of my digital life. It's not ok for it to go down. What happens when payments fail for whatever reason? Shit happens. Should I regress to making up passwords on the spot and writing them down?

I'm very happy to pay $50+ every year or two for a password manager with great UX and cross device support. It is not ok if any functionality is contingent on a subscription though. I really like the Jetbrains model, where if your subscription lapses your software just keeps on working — no updates though.