Based on that design philosophy, where the brand character has to be preserved to that extent over solid engineering should preclude any right thinking person from choosing a Sportster. And that's without addressing all the other naff styling influenced engineering compromises.
You really can't blame Hardley Movinson for giving their customers what they want.
There are motorcyclists, and there are Harley riders, the two have very little in common.
I rented a Harley a few years ago, an 883 sportster. What was eye-opening was the conversation with other Harley types (they come up and talk to you if they think you are in the "club").
Among the knowledge nuggets:
"Jap (or any other racists term) bikes are cheap junk"
" Those Jap bikes front brakes are too strong, they'll throw you over the bike"
" they are so quiet because Japanese hearing is sensitive to low sound frequencies"
(BTW, the sportster broke on day two, otherwise, worst bike I ever rode, so I now am definitively opinionated).
The reality is that Harley has more major safety recalls than all other brands combined. They are the General motors of bikes. They make more profit per bike than any other brand, including BMW, and they source hidden parts from Asia (which increased their reliability), and now rely on European and third parties for new bike development (which is good).
The good news about Harley is that it is run by a savvy CEO that realizes that the typical demographic of Harley sales is dying off, or is far too old for a sustainable business plan. This is why you are seeing the small, cheap Harleys and the LiveWire Project.
If I were to buy a big V-twin, I'd buy one done right: the Yamaha MT01.