I have two coworkers who are multiple truck owners, have hired drivers, but spend their own time driving UPS tractors.
I have friends who are O/O, and I definitely wish I was driving the flashy, loud, custom rigs they have, but my brown Mack looks a lot better when my friends are doing in-frames, replacing turbos, getting harassed by DOT, etc.
I pretty much gave up any dream of being an owner someday when one of those coworkers showed me a $42k wrecker bill from when one of his drivers rolled a truck and trailer.