How many times you run it has no bearing long term on your bottom line. The reasons you do it or don't do it should be based on skill edge, bankroll, table image, opponents tendencies, and how it's perceived by the other players.
If you are short on money to rebuy, but the game is really good, you probably want to run it multiple times.
If your better than your opponent, you generally should let them decide as it keeps them in the game and coming back to the game.
If you want your bluffs to get through more often, then having people know you only go once can help against some players.
If a player is more willing to get it in with a draw if they know you ruin it multiple times, then you might want to run it multiple times to encourage them to get money in badly.
Personally, I run once post flop if the pot is heads up and under a certain dollar threshold. I tend to run multiple times if multiway. And if all in pre, I will generally run twice. Just my preferences. But I'm willing to run more than once in certain scenarios with certain players.
I don't think it's necessary to take an "always" or "never" stance with running it multiple times since it doesn't change EV.