I haven't ridden much since 1983 or so and I bought a Chieftain. Took 2 minutes in a parking lot and it was like I never stopped riding. I left the dealer and had to take the E-way 40 minutes home. I personally think refresher courses (motorcycle, firearm, etc) are a complete waste of money for the average person with common sense who is already familiar with biking/firearms to be told things I already know... but hey, your mileage may vary. I wonder how my father/grandfather and the rest of the clan ever survived in the hills of WVa not having a class on riding a motorcycle, or classes on firearms and hunting. Anyway...about the bikes...
The Classic and Vintage have longer rakes so they are a tad longer than the Chieftain - and handle a tad differently. But all three bikes are exquisite machines. As a returning rider, I was going knowing I was going to take the Mrs on rides and since the Chieftain is more forgiving around turns, I spent the extra and bought the Chieftain with the Stage 1 exhaust and tall back rest with the plan of buying the "wanted" accessories later. The Chieftain really does not feel like a 850+# bike, in fact as I'm sure you've read, it handles like a bike several hundred pounds lighter (seriously). Good luck - don't forget to look at the Chieftain! If you don't plan on riders, that Scout looks pretty amazing!