Well I have otr experience, just not as an oo. I've been contemplating buying a truck and in the future adding more trucks, but listening to everyone else buying even one truck would be a bad idea.
Again not necessarily. Think about this for a min.. Your asking questions on the Internet to a group of ppl that for the most part think our little world is flooded with trucks now. And that very well maybe the case to many of us for the amount of work we have. When I first read your post I thought I read no experience.. After rereading twice and seeing you have OTR experience that tells me you know something about it.
So back to the this thinking thing...Without knowing you, Would I want to see you bring 5,trucks to where I work? Properly not.. If and when I know you would I want to see that and would I help you in anyway I can..More then likely. Its a chance you gotta take..
1 truck? Jump in and try it. for awhile.
A Fleet? Head to Vegas first and if your feeling lucky, go from there.