Welcome and good luck! I'm sure I won't be the last one to tell you, but start out by using the SEARCH option on the top menu. I have been involved with LAWNSITE.COM for about a month now, I asked alot of questions at first, but now I spend hours upon hours reading threads from way back.
I would choose the TRUCK/TRAILER route. Now you can place the daily debris in the bed of the truck and all your equipment on the trailer.
As for the medical/health insurance route....can't suggest anything at this time for you, I'm a solo and my wife carries my medical insurance.
So again I wish you the best of luck!