I'm not sure how you'd get that fine-grained when syncing with a normal file syncing service. That said, I'm generally not modifying entries in my password man

I'm not sure how you'd get that fine-grained when syncing with a normal file syncing service. That said, I'm generally not modifying entries in my password manager on two machines at the same time, nor am I dealing with long periods without connectivity, so I've never found this limitation to be a problem. The bootstrapping problem is an interesting one. Instead of just having a master password for the password manager, you also have to have the file sharing password as well. Like you, I've somewhat accepted this situation. For the home fire scenario, offsite backups are the answer. When you restore your backup (likely with yet another password involved!), the recent-ish local copy of the password database will be restored with it and you can use the passwords stored in that to bootstrap the syncing process. My current offsite backup regime is just a pair of portable USB drives. One is at my office, the other is at home, and I rotate them weekly (COVID messed this up). There are many other ways to do this - cloud services, a NAS sitting at a friend's place, external drives in a bank safe deposit box, etc.