Retiring Pilot requests some info

I wouldn't worry much about tuition reimbursement, chances are you won't stay with whatever starter company you choose long enough for it to mater much.
Higher pay is something that will be hard to get to in your timeframe, specialized work like oversize/heavyhaul and some other jobs that pay well will all present the same problem.
They hire well experienced drivers and the demand for those jobs is high so rookies don't stand much of a chance.
You might be able to get a job in the oil fields of ND and make good money but even that will be tough just out of school, figure on at least a year before you can get away from starter companies and into a better gig and even then don't expect to make a lot of money.
Your 6-7 years is about what it takes to get looked at as an experienced driver but far from enough to be considered an old hand so those top notch jobs will still be elusive and you'll be wanting to retire.
Wish you the best of luck, I started at age 54 almost 3 years ago and I've come a long way but I still consider myself pretty much a rookie to some degree, not totally green anymore but still learning.

 

The best money is tankers and then flatbed.
Comcar hires new CDL grads for tanker & flatbed.
Rinaudo Enterprise Inc. (heavyhaul flatbed in Jacksonville), hires new CDL grads.
Prime Inc. hires for flatbed & tanker (ask if you're in their hiring area)
Schneider hires new drivers for tanker.
Melton Truck Lines hires from Roadmaster & it's one of the top flatbed companies in the USA.
Cypress Truck Line is a Florida based flatbed company that hires new CDL grads & has a terminal in Jacksonville.

Check Careerbuilder and Indeed websites for who's hiring in your area. Ignore "experience required" and apply to any company you're interested in.

Yes, get hazmat/tanker endorsements TWIC and passport(which you probably already have the passport)

 

Look into expediting in a straight truck . No experience is necessary if you have a Class B CDL and can pass the road test. You hire at full pay without 4 to 6 weeks with a trainer. Check Panther Express.

 

System Transport runs 48 states, Canada, Alaska.
It's a flatbed outfit.

trans-system website.

 

Captain Bob:
There are a lot of really good companies and bad one's as well. Knight Transportation has a training program now. CR England is a bad move. England stands for Every new guy leaves after ninety days. CRST has a new pay package but it doesn't apply to newbies, only senior level drivers who they fear are going to leave, so they are giving them con job money to stay.

FFE or Frozen Food Express based out of Lancaster, Texas is a good company from what I am told. Pretty good training program. Prime isn't bad if you can get past the 62 mph trucks. You will be going OTR for atleast a year or more because most local companies won't hire someone who is not proven.

Flatbed is good because you don't load or unload, just tarp, chain and strap. TMC has a training program if you get your Class A first. Hope this helps