Lilbear (and Wife),
First off, welcome to the forum. It was just over 2 years ago when I started researching this website to find out about expediting. Mike was an OTR driver and I had been working as an office manager for an environmental consulting firm (25 years total time in an office), but we wanted to spend more time together and he thought that expediting might be the route for us to go. He found out about this website and I spent 3 months reading, researching, asking questions and talking to people in this industry. Needless to say, we have learned a lot in the 2 years we have been expediters and are still learning.
To start with, driving for an owner is the most sensible way to start in this industry (as most everyone will agree). You may find that you don't like it after a few months and should you "jump in" with your own truck and find this isn't what you thought, you are now stuck with a truck that may take months to sell. Since you have already decided that you will drive for an owner, make sure that he/she is reputable. There are so many owners that will tell you one thing, knowing that he/she is full of crap and before you know it, you are being nickeled and dimed to death. Ask for references and talk to others that drive or have driven for that owner. I have read and talk to others that have been burned by owners.
You will find that many owners will either have you pay for the fuel, tolls and workers comp (60/40 or 70/30 split) and others will cover those costs and pay you 40%. In any case, make sure that the owner pays for any repairs/maintenance to the truck and if these repairs/maintenance are needed, they will pay for it (by credit card or Comdata) rather than you paying and having to get reimbursed (as some owners have not reimbursed these charges back to the driver(s)). Should you opt to pay the fuel and tolls, these are expenses that you will be able to deduct from you taxes.
Another key to this industry is the carrier the owner is contracted with. Are they with FDCC, Panther, LandStar, etc.? As you will read or already h
As others have said, you can go back and research the forum for many of the answers (particularly healthcare costs) you are looking for.
Mike and Cyn