Speaking as someone who owns a 64 panhead and owned a 72 ironhead (rebuilt both from parts): Harleys have almost always been inferior bikes that have a strange sort of charm. Realistically, they occupy the same place as Ural, outdated bikes that have appeal mostly for style. The last time that Harley had anything cutting-edge (ignoring Buell) was likely the knucklehead, which was developed in the 30s.

$8k will buy you a used one (not new), but there is a damn good reason there are used Harleys with essentially zero miles avaliable everywhere. I have fun riding my antique crap, but the new ones are such crappy bikes for the money. A new BMW is the same money, for a more comfortable bike that is less maintenance cost. However, I used to live on the route to Sturgis for most of Colorado, Arizona, and western Texas, and I saw probably 80% trailers vs bikes. People don't buy them to ride them, they buy them to fulfill their midlife crisis.

To further derail, I would argue Jack Daniel's, Levis, and REI are in the same boat- they are grossly overpriced compared to superior competitors and mostly trade on name brand and perception of past quality.