Is now the time for a change? Should I go Over The Road?

This is good information Flatbedder, I always thought your job would be very interesting and fun. Thanks for shedding some light on it. Sorry, but I have no experience with the companies you posted. Good luck driver.

 

For dry van, I'd look at;
Ozark Motor Lines
Danny Herman Trucking - no Northeast runs.
Raven Transport
Milan Supply Chain Solutions - Click here for more info > Apply On Company Site
UPS Freight Truckload - Click here for more info > Apply On Company Site
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Ashley Distribution Services - Click here for more info > Apply On Company Site

• Tuition Reimbursement - up $10,000 for Bachelors and up to $3,000 for Masters
• Scholarship opportunities - for students of Ashley employees

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National Carriers is refrigerated and they have a habit of passing on the good runs to teams. They might give you a long run, then after you hit the interstate, you get a message to go to some truckstop and meet a team there and swap trailers.
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For refrigerated, look at:
FFE (Frozen Food Express)
Freymiller - www.drive4freymiller.com

 

What are the odds of negotiating better terms with you current employer?

 

Abilene Motor Express is a real good outfit:

 

If you have connections in entertainment, you would think of large cars and special trailers going to venues. Supporting a tour for example. You will be driving OTR but at the same time you will be standing by (Hopefully with pay) in your big sleeper until the venue is reloaded and rolling to the next city. You obviously can keep secrets about celebrities and so on. ive run into a few in my time. Little bit of stardust I say.

You will have feast and famine in trucking. Some days or week or more you will sit. Espeically if you loud mouthed dispatch over something and they are giving you rope to quit by making you sit a week. Or longer. (I had that happen once. Maryland ruled in my favor because employer has work, did not issue any work to me and ensuring I cannot maintain ability to work and quit for cause. I got black listed from that company but it's still a victory for me. I lost nothing.)

Anyhow anything is possible but economically, trucking is the easiest way to make and lose money. You do what you can to have savings on every load you run in trucking because if you do not? Then when you do need money it's not there.

 

Best to call each company and ask. All the ones I listed hire Mississippi drivers and some may have Southeast Regional positions.
Big-M Transportation in Mississippi stays eastern USA, I think. They do a lot of Northeast runs though.