I've had a 150cc scooter for the past 8 years, I still enjoy the heck out of it. I used to do road testing for a scooter magazine, so I've ridden my share of scoots. I've also ridden several bigger bikes, and have enjoyed most of them for what they are.
My immediate family likes "real" motorcycles, cruisers primarily. My brother has an Ultra Classic, and my folks both have Shadow 1100s. I'd love to go on some rides with them where I can keep up or go on Interstate highways.
I don't have any desire for a mega-tourer or cruiser, and most of my riding will still be on back highways, though I would enjoy occasional out of town trips. The modern Triumph Bonnevilles are sort of my benchmarks. Something you could ride about anywhere, especially with a few well chosen accessories.
My initial budget will be about $1500-3000, which pretty much rules out Bonnies for the time being. So far, I've found a few Moto Guzzis I like...low mile V50s and 850 T3s. I also dig BMW K75s, and the rare standard version is pretty sweet. I've also looked at the Honda CX series. Barring the Guzzis, none of these are what I want aesthetically, but they are all reliable bikes that can run a long time and should require minimal maintenance.
Any horror stories to be aware of on these bikes, or one to look for in addition?

