Hey CJ,
I know there are companies out there that provide assistance in navigating the regulatory and paperwork nightmare of obtaining a 135 certificate. I don't remember any names specifically but I looked into a very similar operation as you are talking about for a general aviation management course and found that there was lots of assistance out there...for a price. Just google it and you should at least have somewhere to start.
As far as market research, I'm sure you can either find a private firm to do it or look into the FAA planning documents. They typically forecast the demand for various categories of aviation, including 135/on-demand. Would at least be a place to start. Hope this helps.
PS If you are having trouble finding pilots you know where to find me
