Hear me out, it all makes sense.

Okay, background. Several years ago, I lost my poorly-paying job, so I went and made a big mistake by going to Swift's driving school. After quite a bit of time, getting $200-300 paychecks, I left and went to Werner to drive on the Family Dollar dedicated account, out of the Ashley, Indiana DC. Did that for over a year, was accused of damaging a building by a FD employee. (Not even an assistant manager)
I took pictures of the damage, as well as proof that it couldn't have been done by me, because "CYA"....
Fast forward a couple months, I had been told we were losing the account with FD, and this was reflected by the number of Smurf trucks at the DC. So, I jumped ship and went to the OTR side. Less than a month on the road, I get routed into a terminal to talk with safety. They bring up the damage to the one store, I show them the proof it wasn't my fault. "Well, Family Dollar confirmed it, so we need to let you go."
Long story short, I got sent home on a bus, and decided to get out of driving for a while. I spent that summer on temporary active duty (I'm in the Army National Guard), started college that fall for Industrial Mechatronics (essentially factory maintenance), and picked up a part time driving job hauling a 48' step deck. That didn't work out too well in the end, so I picked up a factory job working nights. A few honest conversations with maintenance, and I realized I'd make more money driving truck, even after a couple years on the job.
Got hurt on the job a few weeks ago, right before Christmas shutdown. Healed up now, back to work. Our unit is preparing for a short deployment overseas, less than a month. For that, I needed to make sure my drivers license didn't expire while I'm gone. I'll be overseas on my birthday, so I went in to renew it. During the course of moving around, I misplaced my original DOT medical card, so I had to drop down to a chauffeur license, rather than my CDL-A. Once I can find a place that doesn't want exorbitant amounts of money for a physical, I'm getting my CDL back.
Now my GF and I are wanting to move downstate to be closer to her parents. That's always been our plan. Right now we're in Gaylord, middle finger of the mitten. Mount Pleasant is where we want to end up, most likely. I see all sorts of driving jobs downstate, but only a handful are available up here. By handful, I mean I can find two that will hire for OTR. Halvor, and Roehl, but I don't really want to do flatbed, which is all Roehl will hire for in Gaylord.
Cliff's notes. I have 23 months experience driving, clean MVR, two misdemeanors way back in 98 and 03. I live way up north, moving downstate within the next few months, once we can save up for the moving expenses.

Anyone have any advice? I don't really want to jump around jobs any more than I have to, although I know that's the status quo in trucking. I'm also considering becoming O/O within a few years, NOT with a lease.

 

Northern Logistics requires two years experience, last I had checked. As for the GR companies, I'm less than impressed with any I've found. I've only run paper logs one time, driving the step deck. Hated it with a passion, I've always liked electronic logs. I made decent money at Werner, running fully legal. Not to say that coloring books "make" someone run illegally, either. My main reason for hating them, my handwriting is best described as "epileptic chicken."

 

Like I said, stability is what I'm looking for. Part of the reason for wanting to stop driving the first time, my then-wife was spending all the money, and I was wanting to work on the marriage. Yeah, that was a failure on both parts. My current GF, we've been together over a year, her dad is an O/O, and I have to almost beg her to spend any money on herself... .

 

http://www.truckdriver.com/trucking-company-directory/ShowDOTCo.cfm?CENSUS_NUM=2113977
This one???

 

No, I'm locked into this state, per my contract. I'd have to repay my bonus, if I went anywhere else. This contract goes until October 2020, and even then, I'm only 18 months out from my 20 yr letter.