a matter of how deep one's pockets are and dependency. I admire those who can do most everything on their boat. Practically speaking, I know my limits and get help when I'm over my head. Also, it's often the case that being able to do projects on the boat not only require a particular skill set but also particular tools / equipment. Sometimes the cost vs frequency of use vs stowage space/weight consumed makes a lot of things more practical to hire out.
That being said, my 'next' boat will be far simpler with fewer systems to crap out and fewer to maintain, either by myself or by someone else. It's both a money thing and the fact that I don't want 'broken stuff' to keep me from sailing...