Before you enter a career in expediting you need education just as you would to enter a career in mechanics or accounting. You should spend many many hours in the classroom, i.e. the general, newbies and recruiter forums on EO. You need to read back a couple of years in all 3. That doesn't mean every word of every post. That means reading every word of those threads that appear to apply to you and your situation. That will answer many of your questions and will also create some new ones from things you learn from your reading.
With any reputable company you'll do applications, drug tests, go to their facility for orientation and after that possibly never go to the office again. You'll also be welcome to stop by as often as you like. There are many great companies that are part of the EO community. That said, every one of them has warts as well. The key is finding the company with the warts most compatible to you. Among the suspects, in no particular order and not a complete list are, Fedex, Panther, Express-1, Landstar, Tri-State, PTL, TST and Bolt.
Take good notes as you read, just as you would for any college course. Build your "suspect" list as you go along and when you've completed your "basic degree", reading back at least one full year, then put your list into a preliminary order and continue working on your "advanced degree", reading back the second year. When that's complete take the list of questions you've compiled in your notes and contact the companies to fill in the remaining details and to confirm all the answers you believe you got in your reading. Good luck.