IMHO: Add Intruders and older Shadows to the mix of Viragos and Vulcans and you have a rogues gallery of great handling, often under-ridden and under-valued bikes out there. Personally, I think the Intruder were some of the greatest looking and most honest cruisers ever built — and they handle great. Same goes for the Viragos, but the styling either works for you or it really doesn’t.
As for your riding area, you hae two things to consider. The first is altitude. Some folks are going to tell you that for high altitude, you need a fuel injected bike (vs. carb). While EFI is better at seemlessly handling altitude changes, the good news for you is that you are aleady at high altitude. A carb adjusted for your local pressure should be able to tackle Vail or Manitou without issue. Where carbs “can” get really messed up is coming from sea level and then hitting those elevations.
As for offroad – there’s an old saying that you can take ANY motorcycle off road once. Whether it survives to do it again is something entirely different. Your listed bikes have a few benefits when it comes to limited dirt roads (I’m talking campground dirt roads) and that includes a lack of fragile plastics and a relatively neutral riding position that allows maneuverability that isn’t quite as natural with extreme foot-forward cruisers.
On the other hand, if your goal is to really ride some cool trails, you may want to set aside the styling and look into a dual-sport. There are some great models out there that might be perfect for you.