I'm still a total noob myself, so I guess take this with a grain of salt, but here's my anectodal experience.
I took a few hours of lessons before my MSF course (MSF is still in a couple weeks...d'oh) and not all of my gear had arrived. I had gloves, a helmet, a light leather jacket, docs with steel toes but they were more half-boots and didn't completely cover the ankle. I was wearing regular blue jeans.
I low-sided while practicing swerving. The gloves got torn to shreds (so my hands probably would have had I not had them) and i banged up one knee though not too badly. Surprisingly, the jeans were fine, though they didn't offer much in the way of protection.
I took that as a sign that a small investment in protective gear was well worth it, even if it's the difference between a minor injury and none at all (I'd have been completely unscathed had I been wearing a little more gear). I ordered a pair of Joe Rocket Ballistic 5 pants for about $130.
As for how to learn, there are definitely people out there who are self-taught or learned from family members. The statistics seem to suggest (as much as statistics can accurately suggest anything) that taking an MSF course reduces your likelihood of a crash -- but more important than those numbers is the fact that there are experienced riders out there who will tell you that they picked up a trick or two in an MSF course. Unless you are really conservative on the budget (in which case I'd probably wonder why you were looking into biking with an up-front investment of about $1000 in gear and parts) I can't think of any reason to skip the MSF. Even if you already know everything, you'll get a break on your insurance, and in NYS the MSF course substitues for the DMV road test -- reason enough here in NYC, anyway.
As for a beginner bike, I just bought a Ninja 500, and I don't think I'd call it a crotch rocket. I've heard it described as a "sport standard," and while I would eventually like a dual sport setup, the Ninjas are recommended because they're very easy to maneuver and powerful enough to get you anywhere you'd want to go while not being so powerful that a little extra wrist will send you into the stratosphere. The seating position on a Ninja is only pseudo-sport style as the pegs are really in a standard position and not behind you like a "true" sportbike.
Upstate NY has a pretty good sized biker community, so I'd hunt around for some local or regional boards for advice on things like storage and inclement weather gear as it gets pretty nasty up there (I lived in Ithaca for 6 years and you guys have it a lot worse than we did!).
I'm honestly in the same boat, though -- I didn't want a hog or a crotch rocket and I'd like one of these one day:
http://www.suzukicycles.com/Products/DL ... fault.aspx
I took the advice of people on this forum and bought a used, easy-to-learn bike, but from what I gather, a lot of Ninja riders (and similar bikes like the GS500) are happy enough with them that they never have to "trade up."
I'm jealous that you have a 2-car garage -- I just asked a nearby garage here in the city how much it'd cost for motorcycle storage and they said $211 a month.
