I demo'd a Chieftan and Vintage at Biketoberfest in Daytona a couple of weeks ago. I wasn't impressed.
The Chieftan fairing is not attractive and seems incomplete, almost an afterthought. The gauges are small, the radio speakers are crap, the only good thing about it is the adjustable windshield. It was about 83 degrees with a light wind, but there was a ton of heat coming off the engine on the left side (both Vintage and Chieftan.) It kind of felt like when there's a strong crosswind blowing the heat through to one side. But this was on both bikes and was constant through the 20 minute rides no matter what the direction of travel.
The engine is smooth until load is applied, then it picks up a rumbling vibration. I'm not sure how that would be on a long day at speed. The tranny has a whine in almost all of the gears and has a louder clunk on shifting than any Harley I've ridden.
I didn't get a chance to ride a Scout, but I'll pass on the Indian baggers.