Play until either bending is inhibited by the string running in slots and so being hard to bend, or by "choking", or, on the other hand, the guitar starts to be more than usually out of tune going up the neck or when using a capo (if you use the capo properly - the "Fielding" method described elsewhere on here).

Then fret dressing should solve the problem until next time.

Refret when the frets are so low that getting a clean note is a problem.

IMHO frets are getting softer these days. My late wife's Hagstrom J-45 did not need fret dressing for 30 years - but it came with tombstone frets not round-tops.

It would be normal to get a couple of years to a fret dress, and three fret dresses before a refret.