We've been bootstrapping (successfully) for a few years now and so far almost every instance of using a freelancer failed (some more miserable than other) and cost us money and time.

We're in a unique situation where we outsourced for lack of time and not skill, which is a double edged sword...

My two cents - if you can do it then do it. If you can't, and can't learn fast enough, then try to freelance it.