I'd say it depends on how you feel about accomplishing things yourself vs "having" things. If you enjoy the feeling of accomplishment of mastering (or at least becoming marginally proficient at) new tasks by researching, trial & error, and working through the problems of building step by step then you may be frustrated seeing the results of someone else finishing your project for you. On the other hand, if you get more enjoyment out of having the project "done" to the extent you can drive it to events, sit in the garage and look at it, or whatever brings you the most pleasure relative to that vehicle, then becoming a check writer is the answer. I'm finding that I get more enjoyment out of the building than "having", but I can also scratch the itch building things other than expensive hot rods. I see the guys who get the most enjoyment out of the building side as sort of the "jack of all trades, master of none" kind. Neither approach is bad, providing one gives credit where it's due and doesn't claim the build when they simply wrote checks to builders.

There's also the money side. A guy may get to the point where the house is paid off, kids are grown and gone, and the amount of disposable income supports a new approach. Nothing wrong with walking both sides of the line if you have the flexibility to either do-it-yourself, or pay as you go. It all depends on what really makes you happy (and keeps Mama happy) in the process.