Lease vs Purchase, Cars vs Freight, all those noob questions...

This seems like a great site... so many places to post; couldn't decide where, so figured the best place was where all the other noobs post too. I've been reading various threads but still have questions.

Having been laid off from my programming job AGAIN, I'm done with that line of work. Time for something I have more control over. I've spoken to one carrier so far and he recommends auto transportation for the best money and least amount of dead-heading. I can start with non-CDL and then get my CDL and upgrade to a bigger truck and trailer.

The questions are this: First, does that sound like a good idea? Second, truck. I'm starting off with my own truck... my 2005 Dodge RAM 3500 dually that I've owned since 2007. Great shape, 123k miles, 6sp manual, etc, etc. I don't want to "wear it out" with this job so I'd want to upgrade in the next 3-6 mos. The debate is between buying a truck and paying extra on the loan so in 2-3 years when it has 300k on it, I can get out of it and into another... OR, going with something like the Enterprise Long Term Rental where you get a truck and pay 22 cents per mile and get a new truck every 60k miles (roughly). Though I've heard they're really backlogged right now. There might be other options but I'm not aware of them (part of the reason for this post!).

I'm thinking of starting off with an older used wedge trailer, 3-car, either a triple axle or tandem duals... depends on what I find at what price. Anything specific I should look for, or avoid? I know to check the brakes, wheel bearings, tires, wiring, etc but anything else?

I probably have a million more questions.. I'll post this for now and keep reading and see what else comes to mind. Thanks!!

Rob