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The idea of Motorcycles as investments seemed to take hold with the Yuppies and folks with excess disposable income in the early 80s around the time Willy and the boys got HD back from AMF and really pushed the reliability of the Evo engine.
Oddly, from a market perspective, it was AMFs mismanagement and poor sales that made the older, shovels, knucks, and pans marketable. Thereby forcing an inflated value on older HD products.
After that good marketing seemed to keep demand, and therefore value up.
However, my life long approach to these contraptions has been; Buy the most bike you can reasonably afford, dress it up like you love it, ride it like you stole it, and when you're done - don't make it too hard for the next guy to get a hold of it.
As far as XC vs Street-Glide, it's a complex algorithm to figure out real re-sale value, because my experience is, the cost of ownership with HD is very high if you intend to put a lot of miles on the bike.
Good luck with your purchase!
