How To Get Started - Companies That Pay For Training?

Brand new here - any help is greatly appreciated. I'm 36 years old single no children. I've got a clean driving/criminal record. I've done a lot of traveling and driving as a touring musician in passenger vans generally and am accustomed to being "on the road." I'm getting older in musician years and am wondering if trucking would be a good way to continue making a living on the road.

I've been looking through the posts and wondered if applying for a company that will pay for CDL training is a way to go? Realistically how long does training take and what kind of work can you expect to get? I see a lot of posts w/folks not getting the miles they'd like and being tied up in truck stops etc.. What kind of money can be made say 2-5 yrs into it? If one finds they really enjoy the life is being an owner/operator a good way to go? What is the difference in the money and what kind of expense can be expected w/buying and maintaining a truck?

A lot of questions I know, hopefully not too much to ask.

Thanks in advance -