At a career crossroads and once again considering trucking (OTR)

Thanks for the input everyone. Trying to understand pathways better: Based on recommendations, I'm sensing that it might be better to get CDL-Learner's Permit and try to get trained by one of the CDL-training companies (and then working for them for the 1-2 yrs) than trying my luck at one of the independent CDL schools and hoping to find an OTR job? Based on what I have read here and other websites there's certainly pros and cons to both approaches but does the current state of the freight economy mean that a successful stint in a large company's in-house CDL school make it more likely to get that OTR placement I am looking for?

That said, if I did training with a large company, how difficult would it be to go back and add endorsements or remove an automatic restriction especially if I am out there on the road a lot?

I definitely understand this is as much a lifestyle as it is profession. I enjoyed the times I have driven moving trucks cross-country for myself or others. I've done deliveries and pick-ups in NYC for work and managed just fine. Obviously 17' to 26' trucks are not the same thing as a 53' tractor trailer. Having never done it before, I do have some anxiety about backing my trailer into a dock with just a tiny clearance on either side!

I know do need to downsize and I would be lying if I said I wouldn't take that higher paying job in one of the fields that I have experience in if it paid over 100K. Or even 80! But if I just am not getting those opportunities in in areas I used to find decent work in, I just need accept that and to find something that could meet financial goals and still interests me.