If you go on a road trip, you don't know what you're gonna get in terms of surf... UNLESS you have some flexibility and can time it for a swell, either north or south. If you know there's going to be waves, you can make the decision at the last minute, and certainly do some exploring and score. If you love just traveling for the sake of traveling, and waves are just a bonus, hit the road. New England is beautiful, but the water will be cold, and although there appears to be a lot of coastline, much of it has limited swell windows and access can be an issue. Going further north, into Canada, is an option and NS is loaded with potential, but again, plan on roughing it. I go north every summer for a week or two, and if I had to move, that's where I'd go.
As for building your own board... you can get away with minimal tools for your first board. You can rent space at Greenlight, use his tools, and get some advice as you go, and your chances of coming out with a decent board are much, much higher. If you want to do it on your own, here's my advice: Build a set of racks in your woodshop, and buy minimal tools for your first board... you can get them all from Brian, along with blank, cloth, resin, and hardware.
PM me if you need a quick list of the minimum tools required.