I feel your pain with the bread route been there, done that, never again.
Its funny reading your story I had a bread route that fell through, worked for a local delivery company and eventually parted ways due to money, and decided to work for myself.
As for starting out with a truck, I'm with davekc on waiting until spring at least after new years. You're thinking smart..Cutting your teeth with a fleet owner is a good idea local and OTR work are diferent animals. This will allow both you and your friend to find out if this is a fit without the investment of a truck. I believe taking friends into bed or business is a bad idea as it typically ends up with disaster. If you decide to go in together, just make sure you and your friend can part ways before it destroys your friendship
A WORD OF WARNING!!!!!! SWEAT YOUR PROSPECTIVE CARRIERS.
Ask the hard questions, and lots of them. Don't sign on if they don't pass the gut feeling test. Also never trust what a recruiter tells you. Its their job to get you to sign on.
Don't go all the way on the first date. In other words give that offer a couple days to cool off and think it through. Im sure after the route you will agree that an attorney should be involved with the decision.
One thing to consider getting is your own operating authority.. Yes you will be on the DOT grid, but if you follow the rules most likely show up less than if you work for another Motor Carrier. This is because you don't have to rely on the MC and their drivers not screwing up. Some carriers don't like working with those with their own authority as they often see you as competition which can make slow times tough if you don't have friendly carrier relationships. Most importantly, all the expenses will be on you fuel, maintenance, business expenses, and insurance.
The pros it opens up more opportunities especially if the leasing doesn't work out you can keep the truck hired through brokers your own direct customers / businesses and the general public. You will also have the final say on when, where and if the truck moves and for how much you are paid.
I mentioned insurance, I would recommend Commercial Insurance Solutions first as they specialize in expediters and they run a good shop. If you need something special like high value insurance beyond the 100,000 on the freight and 1 mill liability and C.I.S. cant cover you, PM me I have a couple contacts.
The cool thing about this site is its a good place to ask questions we share our knowledge whatever it may be, and yeah, sometimes we stir up the poo pot, and on occasions get into a piszing contest on a topic or two.
Welcome and good luck
Bob Wolf