Most of the time I just DIY for anything that’s not massive, but when it comes to big projects like Roof/Foundation you listed Friends/Family/Neighbours I trust who have used them in the past.
Once I find a not shit contractor, I latch on to them and maintain that relationship.
Ubuntu server, it’s a bit more modern than Debian and has a massive install base which means someone has had your problem and fixed it before and documented it.