Yes, every time I want to set it up on a new device I have to import and trust all public keys that it should encode to; and if that device gets its own gpg key then that key also has to be distributed to and trusted at all prior sites. Which isn't very often, but still somewhat regularly (ie. new laptop, new yubikey, formatted hard drive, etc.)

I think it would be a great addition if pass could actually automate this by storing all relevant public keys internally.