The thing that seems to be overlooked in all the defense of HD is that yesterday's old/mature guy isn't todays and isn't tomorrows.
Classic rock has gone from Buddy Holly to Steppenwolf to Led Zeppelin to Van Halen to Pearl Jam.
For a brand to sustain at a certain level it has to recruit NEW customers along the way. Guys in my generation (50's) are arguably the last one that has a direct connection to HD's glory days. We might have seen knuckle heads being ridden around, or WW2 surplus flat heads being customized, and for myself XR750's being ridden hard, fast and loud.
For younger generations it's JUST nostalgia and that kind of nostalgia has always been short lived and comes and goes with pop culture references and associations.
Contrary to what anybody wants to believe, the decline in new bike sales is a serious issue for the MOCO, in spite of selling a larger volume of whatever segment than whatever other manufacturer. For whatever shortcomings we may believe the board members have one thing they can see is a developing problem, regardless of the business they're working for right now.
Harley won't be, "just fine" if they continue as they have for the last 2 or so decades. That road is lined with the wreckage of other companies that figured they were a legacy brand that was too big to fail or their brand image would ensure continuous profitability.
It might be argued that though Harley's trikes are apparently good sellers and function well for what they are they have done a degree of damage to the brand in the eyes of those younger consumers that Harley needs to attract.
Regardless, none of us know whether the planned new bikes and proposed changes in how the company operates will lead to a successful and prosperous future, but we can be certain that for them to do nothing but staying-the-course and tweaking the existing offerings will lead to their eventual demise.