Well, unless your plan is to hedge from the outset, like when you bet multiple tennis futures with a plan to cashout as many as possible when they go deep, it's usually 'bad' to hedge math wise.
But I think we have all been in the situation where we took a cheap parlay only to realize we really don't feel good about having 50x our normal bet size riding on that last leg!
So yeah, I'd agree it's all about how much that money means to you personally.