I have both a Honda & a Harley Davidson. Have always had one of each, give or take a few months here and there.
Two totally different rides and two totally different missions.
I have never had an Ultra/Road/Duo Glide, so as far as a cross country bike, I cannot comment.
I have had a '73 Ironhead Left Foot Shift Sporty and I still have my '95 Heritage Special.
My first bike was an '81 Standard Wing. Then got the Sporty, then got the Heritage, then got a '98 Valk, sold the '81 Wing, sold the sporty, sold the Valk and got the F6B.

I don't dress like a pirate when I ride Saorla, nor do I care if my jacket & helmet matches my bike when I ride Isleen.
I really don't care what other people think when they see me on either one.
If someone wants to judge my contents (good or bad) on the method of delivery? That's so not my problem and I shan't be taking it on.
I'm not the fastest guy out there, I'm not the safest guy out there, I'm not the smartest guy out there.
But I can easily live with my choices and be happy in my own skin.

There is a time and place for almost anything.
Including Harley Davidson motorcycles.