I haven't found boat ownership to be any less or more frustrating than project car ownership in terms of repair/maintenance. They take time, attention, and money and provide enjoyment at a typically lopsided ratio to the repair side of things.
Outsourcing out work on either, by either paying someone to repair your junk, or getting rid of junk and getting something 'nice' is an equation on how much money you want to spend.
However the thing that drives my boaty about boats, is how hard it is to test/diagnose things and if something goes wrong you are stuck in the water....