>Finally, you get to syncing, and the friction is bigger than you expect. It is not enough to set up a LAN folder; your solution needs to be able to resolve conflicts if you ever use more than one device simultaneously, otherwise you run the risk of losing changes.
Would you explain what kind of a problem you see here (I mean: KeePass related)?
AFAIK syncing two KeePass database instances is based on timestamps, so losing changes made on any two copies kept/used on different devices is simply impossible if you properly use KeePass (ie. do merge them with KeePass).
Of course, if you want to have a real cloud-based password manager then KeePass (without any extension) isn't appropriate at all. But what's the purpose of comparing apples to oranges?