Having a hard time deciding how to go about getting my CDL

Alright I spent about 3 hours between yesterday and today practicing docking. I went out into the yard, hooked up a trailer, took it around the building and docked it. Yesterday I did it on the wide open side without other trailers around.
I just now docked one on the tighter alley dock style side in between two trailers. Took me about six tries, but I got it!
I'm really starting to get excited about driving and am building more confidence.

I also talked to our operations director last night and he approved the idea of me driving as a fill-in driver. He also offered to let me use the company truck to test in. He said he would pay me another 2 dollars and hour on top of my regular pay, not to mention the fact that I'd only be really driving after my regular responsibilities are done with, so it's going to be all on overtime when I am driving.
TLDR I'll be getting paid just over 40 dollars an hour while I drive the truck...in other words, if driving as a fill in driver translates into just 5 hours a week, that's a 10,000 dollar a year pay increase, but it's realistically going to average out to about 10 additional hours a week by my estimates.

All of the drivers are telling me I should stick with this company as a fill in driver for one year and then start looking elsewhere for full time driving jobs with my "1 year of experience".

Does this sound like a realistic plan? I'd essentially be getting paid 65-75K for my first year of driving if I did it this way. My concern is that companies may not recognize it as "experience" if I'm only averaging about ten hours a week of actual driving. Surely I would be a better candidate than someone who just graduated from school at that point???
It would be really good experience, because almost all of the venues that we operate at have difficult and close quarter docking situations, and all of our trailers are 53'.

 

Yeah it is pretty scary! I've operated 60' boom lifts for a living doing aerial rigging for a while and this rivals when I was learning on those. I wear a heart rate monitor and it was definitely getting up there lol...oh well, I guess it burned some calories.

I downloaded a driving simulator for my PC last night to help solidify the concepts. It seems to be pretty good.
We'll find out this morning. I'm going to be back at it here once we get started this morning.

 

Now that's what I like to hear! Did he say if it held him back at all?
I'm already getting behind the wheel daily for at least an hour a day and I don't even have the license yet. Today I was able to back in a trailer to the dock 3 times in a row on the first try. They weren't lined up the prettiest, but good enough to safely get the truck loaded.
I can already see how simply getting the CDL will open all kinds of opportunities to make more income. I'm hoping that combined with my solid work history and clean record, the fact that I don't have a certificate from a school won't be much of an issue...