I'm a do it yourself er, but know my limits. I've had the opportunity to hire a few contractors in the past, siding, drywall, tile.
It has never been a 'good and easy' experience. Maybe once.
Showing up when they said they would.
Honoring the estimate
Doing consistent quality work.
Honoring the work of the craftsman coming behind and before.
Any experiences or ideas on how to make it work out better?
Such results would largely preclude one from proffering patronage thereof.
I also usually do stuff myself and I have had very mixed results when I've hired out.
My best advice is to do your homework!
Get multiple estimates and ask around for recommendations and reviews. The times I've been really displeased (like the new windows for the whole house project that was just finished) there wasn't enough research done before selecting the contractor. The times I've been happy (fence put up years ago), I did a LOT of research and got multiple quotes in addition to estimating the materials and time to do it myself.
Let them know you know the local licensing bureau. They can really fuck them up.