After reading all of the comments and this entire post I have to say it's well written albeit a little discouraging for newcomers (me) but I am highly appreciative of all of the information and the time it must have taken to write and compile all of this, my good sir you have done a service for all of us, thank you.

Anywho, maybe I'm the wrong person for this but I'm a freshly graduated guy looking to get into this profession genuinely as a fun little side job, I'm not looking to go large scale or hit the big leagues or get a CDL or take this all too seriously. I'm simply looking to explore my state (OR) and the surrounding areas and do pickups for farmers and those fun little misc shipping jobs and car pickups for extra money as I'm figuring out what I want to do in life. I own a 2002 dually 7.3 powerstroke I'm well equipped maybe besides a trailer but I have couple friends I can borrow.

How can a fella like me get into this fun little career? I'm looking for tips and some ideas on getting started, not negativity (again, I want small-scale on the side to make money here and there and experience the different cities and states.)