He checks, I bet

This has worked for ages, but I have learned to forget about it facing strong regs. When villain is barreling and we’re calling (I don’t like being on defense) and then he checks the river—

He’s calling, so don’t go thinking 2nd pair is good. Against the population, it’s still a good thought process, but don’t stab against good players, just show it down.

I mostly play a small room, so game selection doesn’t apply. I kinda embrace the fact that when the good players show up, I’ve got to beat them. So much of this game involves tailoring your play to the opponent at hand.

I don’t play online, but applying it to poker in general, is there any theory that backs betting when checked to?

Any suggestions on when this is a good move?
Or not a good move?