I'm an MSF RiderCoach, and would have to follow the rest of the crew on the recommendation to start smaller. If this is your first bike.... DON"T GET A WING!!! They are HUGE!!! Easily in the 1000 pound area. The new 1800's are VERY well balanced and accelerate and handle superbly.... for someone who knows how to ride. For a novice rider the biggest I can go is around 800cc's.
The fellow that recommended the Suzuki Volusia is spot on. It's looking like you are going the cruiser route with style by wanting a Wing, but if you are just testing the waters you should get in the shallow end first.
If you really want to have a blast riding... Get 2 bikes... 2 TW200's or GS500's or 250 Ninja's or hell even better see if you can find a Kymco Venox. They are AWESOME bikes that come with a great warranty and are very well built. I have worked in Suzuki, Yamaha, Kymco, Triumph, and Ducati dealerships.... There are a world of choices out there... Review the facts budget your monies, get your gear, take the MSF course FIRST... not AFTER the fact.
If you have any other questions, post em here as there seems to be alot of riders on board or kick me an email and I'll be happy to help you out with getting into the MSF course or getting you some information.
And lastly, I do all of my price shopping through CycleTrader.com You can pick options and prices and what not of what you want and see what the going rate is.... For the record I currently own 5 motorcycles.
Oh and my current riding motto is... "Ride like they can't see you, and if you know they can see you, ride like they're trying to kill you!!!"
Best of luck....
DM