what to get?

Im also In SNH and I bought 2(thanksgiving and christmas dinner) just a few weeks ago Broad Breasted Whites from a feed store. They are hybrids that are bred specifically for meat. They do not breed naturally and do not live long(mature between 4-5 months to process for meat). Perfect for me because I have a problem getting attached to everything lol. So if all you want is dinner Broad breasted Bronze or Whites is the way to go. I decided I like having turkeys so we are going to be buying Bourbon Reds which are a Heritage Breed they are a little smaller breed naturally and live long and make both good pets and good meat(though longer to mature for the meat part(8-9 months). This is all new to me also but Im glad to meet someone in NH that shares some similar intrests.

If you're looking to get Broad Breasted birds for Thanksgiving or Christmas, unless you plan to freeze them, it's still much too early. With the increased growth rates of today's birds, they will be much too big to easily handle and cook by Thanksgiving, and especially Christmas. About August 1 is an ideal time to get a decent sized bird. Go a week earlier if you must have them larger, but much more than that, and you'll have a bird that will take forever to cook, if you have a pan or even an oven large enough to fit it. For Standard breeds (so-called "heritage"), about 6 months minimum is what you want, if not more, so you're a bit late for them at this point.

I did get my BBWs a little early. They had 4 left at the feed store and they were the last they were getting in. So I bought all 4 and gave 2 to our friends to raise. They are already 7 weeks old and we plan to process them in early oct and freeze them. I think July is a good time to get the BBs if you want to process right before thanksgiving and heritage breeds closer to march or april.

As for your other questions

Feed should be a turkey or gamebird starter 28% protein for the first 8 weeks I believe (medicated or not your choice) then there is a grower and then a finisher

Yes they roost and they like to be up high though BBB and BBWs dont roost as much as they grow very large

You can keep as many as you like I suggest just more than one as they need companions

Not sure how old they need to be for winter though I suppose the older the better young turkeys chill easy older turkeys are very cold hardy

SO far mine are not hard to care for but Ive only had them a few weeks. I hear they are hard to keep alive and are very fragile for the first 4-6weeks ish.

Im a newbie so I only know what Ive read I havent had much hands on experience yet.