Plugins installed via the
Get Plugins on the Calibre menu , are pretty solid (many users). If in doubt about an update, just (mostly) ignore the blue 'Update available' until you check in the Plugins thread.
I say mostly ignore, because
oopsies 
happen (even to Kovid) and those need you to pay attention to not trigger the misbehavior or load the fix.
(what I am trying to say is there is no single response to updates. some fixes happen fast, others take time to find, And NOT ALL are the PI Authors fault. Calibre and Plugins are built on foundations that someone else made)
Check here at MR to see if there are issues, Report here if you are an very early adopter and see something odd (warns others). Then decide Wait or Now.
OH! And
BACKUP before you do any BULK task
on the Library