In Cincinnati, Have Wannabe Questions

I live in Cincy and I want to get into OTR Driving. I have a few questions I would appreciate any help I can get with my decision process. My business went belly up after bankruptcy and an accident that broke my tibia I have some savings and I am working as a security guard right now so I recently went through a series of background checks including DHS to get the guard job at the chemical company I work at. I really just want to get out on the open road. I have no wife or kids and I can put my life in storage for a couple years no problem. I just have a few questions so here goes.
1 Which school in my area is best?
2 Do I need Ged?
3 Does it make a difference whether school is company sponsored or vocational.
4 Do I have to retake car test since CDL is a higher license
5 Only thing on driving record is operating an unsafe vehicle in 2002 ( wreck on a HD with sidecar, the sidecar wasn't put on right by dealer, no points. Will this affect me?
6 I have a misdemeaner for menacing from 1991 ( argument with exs BF ) will this affect me? didn't with guard job.
I am studying the cdl manual and taking practice test on line 4 nights a week on crst site and rich trucker site are these really close to actual written test? Any help would be appreciated. I have always wanted to drive OTR just had another gig for 25 years that kept me from it. I am 49 and in fairly good shape. I plan to do this in spring so I have some drive time under belt before winter. Oh one more question:
I have a prescription for xanax that I was prescribed for anxiety when my business started failing but only take now to sleep , It is a schedule 1 , Do I have my Dr. write a note or quit taking now so it is out of system by spring?
Thanks
Roy