Not unlike operating a government, this is what happens when someone who is not at all qualified is put in charge. Just because a person ran restaurants, sold knives, ran casinos, sold cars or whatever,.....does not mean they are the be all end all answer.
Hell, anyone of us here can point out a thousand things he should of done. With his aging (and sadly dying off) target group, HD should have had some basic upgrades by now, like a reverse gear option. With so many of us dealing with replaced knees, hips, shoulders, bad backs or cancer, you would think reverse on a 1,000 pound bike would be a good thing. Virtually every other major touring bike has it, but not HD. And if you say it costs too much, factor it in elsewhere. Change the fancy rims to base level rims. Go with one color paint instead of two tone paint and add reverse.