The smartest Harley-Davidson is usually not the newest one. There comes a point when a Harley bagger stops being an emotional purchase and becomes a genuinely smart one. The problem is that most buyers hit too early, when prices are still inflated, depreciation is still aggressive, and the platform itself may not have fully matured yet. On the other end of the spectrum, going too old can saddle you with outdated tech, dwindling support, and a bike that feels every bit its age once the miles start stacking up.

Source: https://www.topspeed.com/smartest-pre-owned-harley-bagger/