Just to throw another wrinkle in here. The BMW R1200C actually is a very comfortable cruiser and they can be found at a good price. They were never very popular and I have seen low mileage bikes for a lot less than your budget. Some love them and some hate them for the styling, but they are a good do it all comfy ride.
I can't wait for the comments on this one.
84 R100RS LE,14 Ducati MTSGT, 73 850 Commando, 78 CT90, 14 Ural, 74 Eldorado police, 64 R50/2, 13 TR650, 01 DRZ400E, 94 900SS/CR