Driving trucks for my current company to learn VS schooling

So I'm a production foreman at my current job, but I'm lookin to change careers and start truck driving instead. We do a lot of local runs just up the road and have some pretty old, beat up trailers and tractors.
I let it slip to my current boss today that I want to get a CDL. He told me if I wanted to, I could practice driving the trucks here in our lot and when I get the license, I could rack up some easy miles doing local runs for them. Also so of the drivers were pretty enthusiastic about teaching me how to parallel park, ect.

I'm wondering if it's better in the long run to go that route, or pay for school/do paid training? The second I get enough hours to go elsewhere, I'd be looking to change companies. I'd just be using this one to get the experience and learn...in other words I am looking to go to a "starter company" no matter which route I take to learn.

 

Oh I

That's a beautiful machine there! I'd do OTR if that's what it took to get started making some decent money, but to be honest I'd probably prefer being home at least once a week, since I live with my GF. If I did OTR, I think I would want to maybe only do it for 6-12 months to jump start my career. I think as you saw in that other thread, I am leaning toward tankers.

So lets just say I wanted to get a job at Schneider, or some place like it. Would it help to get my CDL by learning enough at my company and passing the test, or would they still want me to learn at their affiliated school? I guess that's mainly what I am wondering. If there's any real benefit to getting your CDL at a school VS learning everything from the drivers I already work with and passing the test.

 

Well, it wouldn't be like official training. It'd be more like " the boss is out today, let's jump in the truck and practice backing into the loading dock!" type of thing. I'd likely show up a little early and stay a little late, maybe do a little on my breaks too. Totally unofficial and under the radar.
Do you think I could get sufficient experience that way? What about passing the CDL class A test? How would I get a vehicle?...best case scenario is I lie and say I want to drive for the company and they may let me use their truck for the test, then just bail right after lol...

At this point I'm kinda thinking maybe just get a bit of practice and then attend school, which should be a breeze once I get some driving experience.