Would This Be A Good Career To Become A Conductor Around The Future?

I would go ahead with that plan with a few cautions. Do not take OTR tractor trailer. you will never get schooling done. Also people with CDLs work at UPS for years before they earn the privilege of driving for them. Also you will find that part time work with UPS does not compare to a full time job although it will get you by. Good luck on the railway deal but if Im not mistaken I think you need a degree in engineering to be one, although they don't do any engineering :/