I'll be honest, at this point and time I'd buy an Ultra before I bought a GW. The fit and finish is just fantastic on the Ultra, and it still gives you the experience of riding a motorcycle. I've ridden a few GL1800's, and they are simply boring. The easy maintenance and repairs on the Ultra are also a selling point for me. I wrench on 99% of my own stuff, and the less time it takes, the more I can ride.
I'm still PO'd at H-D's corporate idiot for what he did to Buell, though. so no H-D product for me for a LONG time.
Buy a used one.
You'll get the bike you want, HDI doesn't get any of your money, and they're so well supported in the aftermarket, that short of needing a complete engine replacement, you'll never have to enter a Harley dealership for anything. Ever.
There is simply no other MFGer so well supported, so thoroughly in the post-sale market. It's pretty incredible, and it should be a serious consideration for anyone seeking a bike of a style that Harley makes (cruisers and cruiser-dressed tourers).
