Not new, but not recently "experienced", but want to drive again.

Too long didn't read:
Been out of the truck since 2018-2019. Came into the office to dispatch and worked up to fleet planner. Now looking to get back into the trucking business on the other side of the wheel.

I guess what I'm asking here, and I know this is dangerous, is for opinions and thoughts. Has anyone done this? Know anyone that has done this? What would be a good company to go through this plan and process with?

So as the summary says, I've been in the business for about 11 years. 4 years on the road and the rest in the office learning as much as I can. The original purpose of getting out of the truck was to take care of some health and family business, and the years just kind of went by.
Now, with some recent changes in the business (my company) it has become WAY less financially stable.
I'm older, wiser, and my wife and I both only have our grandkids and elderly fathers around the homestead and town.

I'm wanting to get back into the truck, take her with me, and hit the road for a while.
Toying with the idea of my own authority, own truck, and own dispatch. But being out from behind the wheel as long as I have been I'm thinking my better bet would be to get some seat time for about 6 months to year then look at long term.
I still would like to take my wife with me, along with our pet, and hang out on the road a few weeks at a time.

I have talked to my current bosses and supervisors, and basically told them, "I need to make more money".
There solution at the moment is to have me run some day runs in our local region one or two days a week, and train to install ELD and camera equipment along with my daily office duties. I'm leery of that, as I don't want to get into the rut of just doing tech stuff and still office stuff. And I don't fully trust some of the supervisors.

I don't mind working. At my age and how I was raised and grew up I'm not afraid of the hours or work. But I'm not positive this makes it towards my current goal.

 

It'll be a cat. She's an elder cat, not that would really make a difference.
I'm in and around the Asheville, NC area.

 

Oh I get that. That was why I was thinking Company driver for at least a few years to see how things settle out.