For shopping, try what I do (since you said your wife is supportive), take her with you. My wife and I will go out shopping, and the thought in our head is we are shopping for "my twin". It helps alleviate any stress if we are a bit away, she'll hold something up and say, "I think Val would like this," or I'll ask her opinion on if something would look good on me and say, "Do you think Val would wear this?" Our local salvation army has a 50% off on Wednesdays, and there are really nice clothes there, so I've gotten quite the selection in just 2 trips.
As for the razor bumps, my thighs get them bad, but I found that by soaking in a tub of hot water and shaving recalling helps open up the pores to remove the follicles without so many ingrown hairs (razor bumps). Also get a good lotion/moisturizer to put on afterwards too. It's very pricey, but I have some called Vine Vera I had gotten my wife when I was on a business trip to SF a couple years ago (it's all natural, but we have recently discovered my wife is allergic to the entire planet since, so she has to be extremely careful now).
For support groups, Boston area should have a good selection. There is a huge community up there, and my friends brothere is openly gay, and they go to all kinds of bars/clubs together, and never have any problems (his brother wears drag queen style makeup daily too). Just Google the area for transgengered groups, and also maybe try contacting a transgender therapist's office, to see if they can give you any assistance.
Good luck,
Valerie (TBD)