Re: Island Packet and Cape Dory 33- 40 range.
I crewed on my friends CD30. Awesome boat IMO. We sailed mostly on Pamlico Sound and sometimes out to open ocean through Ocracoke Inlet. Not the fastest boat but felt very comfortable even in heavy weather and short, nasty chop on the Sound. IP boats look awesome to me as well. If I could afford one I would be seriously thinking about buying an IP27. I like it more than CD30 for coastal cruising (draws only 3.7 feet and has wider beam and more room than CD30).
Be kind, for everyone you meet is fighting a hard battle.