**WARNING! Long Post Ahead!**
The fated moment is arriving. Since I'm graduating soon, I'm getting a motorcycle as a gift for myself for all my hard work

So I'm summoning all the pro Bikers of n00bfest for your opinions. Of course, I have quite a lot of questions which I'll keep posting in this thread.
I have never even sat down on a motorcycle before, so I'm as n00b as it could possibly get. I've been reading up a lot on different types, beginner specific ones, insurance issues etc. After doing an extreme amount of research, I've come up with a list of candidates. I'm leaning towards a used motorcycle because everyone says that I will drop it no matter how careful I am, so getting a used one will be less painful when it comes to repair costs.
As a complete beginner, I want to stick with 250-500 cc bikes, and in exceptional cases, 750cc (this depends on how I feel after trying to maneuver one).
So in no particular order, they are:
1. Yamaha v-star 250 (cruiser) : 250cc

2. Kawasaki Vulcan 500 (cruiser) : 500cc

3. Kawasaki Ninja 250 (sport) : 250cc

4. Buell Blast (standard) : 500cc

5. Kymco Venox (cruiser) : 250cc

6. Hyosung GT250 (standard) : 250cc

7. Honda Shadow Spirit (cruiser) : 750cc

8. Honda Shadow Phantom (cruiser): 750cc

Out of these, my dream bike is the Shadow Phantom. Unfortunately, I think that 750cc along with the 550lb weight might be way too much for me to handle at the moment. I prefer than phantom over the spirit (it just looks awesome), so my plan is to get another bike right now, and go for the phantom in a few years after I've gained enough experience. The other problem is the price (~8k+). The only thing I dislike about the Shadows is the dual pipe setup on one side. I like my bikes to have a good symmetrical look
Here are some more details. I'll be using the bike primarily for fun and randomly going to college/work etc. Most of the time I'll be going around Staten Island (where most of the drivers have an iq < 50), but I'll also be taking trips to Jersey, Brookyn and NYC and generally all around NY every now and then (ie more regular traffic and less highway).
Power is not an issue for me. Even on my car I rarely go past 75 on the highways nearby, and I'm not a speedfreak.
G-man recommended the Shadow Spirit, but that and the Phantom (which I like more than the spirit) maybe too powerful for me at the moment, and are ultra heavy (I'm not exactly in the greatest shape right now). I keep feeling that I will drop it when I come to a complete stop or when moving around in a parking lot. So I'm leaning towards getting the Phantom in a few years as I mentioned above, when I'm an experienced rider.
Insurance - This one is a pain. Complete coverage is out of the question, because due to my inexperience and location, 250cc-500cc cruisers cost ~$1100 per year for complete coverage. For the Ninja 250, that's ~$3500. It doesn't change that much even with MSF + defensive driving discount or even if you already have a car insurance for the same company, so I'm opting for the bare minimum coverage (which may or may not be a good idea).
So with minimum coverage, the sportsters (Ninja 250) come to around $650 and the cruisers (250-500) come to around $400 per year. Though I've heard of people paying $50-100 for full coverage outside NY, those are rates I can manage (since I don't have a choice).
I've heard people say that the ninja 250 is the best beginner bike out there, but due to the extra insurance and because I don't like extreme high rev bikes (or the scream), it's the least likely candidate, after the Shadows.
Right now, one of the dealers nearby has a good deal on a used 2009 Yamaha V-star 250 ($2k). I like the looks and sound, so I'm leaning heavily towards buying this one before it's gone.
There are some nice used bikes on ebay and craigslist, but since I have no mechanical knowledge or bike exp. and have no friends who have bikes either, so I don't want to go that route to avoid getting ripped off.
Another problem - I live in a side apartment of a house, so there is no garage. I need to find a way to protect the bike from snow and heavy winter, so I'm looking for some heavy duty covers that'll provide some excellent winter/rain/snow protection. I saw some "portable shed" type covers, but they cost too much and I doubt the houseowner would let me put one on the extremely small driveway.
So right now, I'm thinking about grabbing the '09 Yamaha v-star 250 before it's gone and play with it around the block, and take the MSF class when it opens (feb-march) before taking it out on the main roads. If I could find a good deal on a Kymco Venox, I just might go for it because that is the best looking one out there, except for the phantom.
I'm 5'8 and 190, so the bike needs to be one I can handle quite well.
So, let the wisdom flow

Also, if you got bikes, post some pics for us to see!