I rarely re-enter because my attitude is "there's always tomorrow". I am in no hurry to win!!! But I should also admit that I don't play poker to make money, I play poker because I love playing poker. Money is not a priority for me at all. I know that makes me a bit of a weirdo.
I don't want to embarass anyone so I'll keep this story generic, but I recently watched someone make 16 re-entries into a tournament that only paid 8 buy-ins for first place... so even if that player won the tournament, they would have lost 8 buy-ins. But they didn't cash at all and lost all 16 buy-ins. It was painful to watch but that player did it to themselves and deserves no pity or sadness. I just couldn't understand what goes thru the brain of someone like that, all I can guess is that they have an addiction to the action and just don't care about profiting.
From a practical standpoint, I might re-enter one time if I bust early and am still excited to play in that tournament. If it's a bigger prize pool for instance, that can influence my re-entry decision, but I'll never be one of those players who does 5 or 6 or more re-enters. I just don't think that is wise unless it is a very special tournament. I don't play for the money, but that doesn't mean I am un-wise about my bankroll, I guard it just like someone who does depend on their poker income to survive. I'll close by repeating myself - there's always tomorrow, or there's always next week! Rather than re-entering a bunch of times, I will just wait instead.