1) PVD often has better deals (b/c Southwest often drives prices down) and is smaller and pretty nice. BOS on the other hand is pretty big and the construction can be pretty tough to navigate for those not experienced. In addition, the traffic on say a Friday afternoon down to the Cape is absolutely atrocious. All things being = and not being from BOS I would fly into PVD.
2) I would say absolutely do not take a car over for a day. Most ferries go into the large towns Oak Bluffs or Vineyard Haven. I think there may also be one into Edgartown. I would take bikes (that's what me and Ms. Chobby100 do for a trip that is a few days). Check out
http://www.mvol.com/
3) I love the Vineyard. There I would say check out the towns of Oak Bluffs, Edgartown and Vineyard Haven. "Up Island" Menemsha and Gay Head are great. We always take our bikes over the "On Time" to Chappy and ride and go to the beach there.
4) not real sure, but try
http://www.capelinks.com/
http://www.mvol.com/
http://www.mass-vacation.com/jsp/index.jsp
http://www.fodors.com/miniguides/mgr...s_vineyard@617
http://www.fodors.com/miniguides/mgr...on=cape_cod@44
5)
Restaurants on the Cape or the Vineyard? or Both?