I've found HD's quality control and reliability on the new bikes to be comparable to any other brands myself. The bad old days if they really were that bad are long gone. In my personal experiance owning Harleys over a 30 year span I would say I've been very lucky with them, more so than the few Hondas I've owned.
On the weight issue you may be right, the Sporty is a porker as befitting a 50 year old I guess, not sure how the Yamaha plays out on that one.
I think the dealer experiance is what you make it, granted I deal with the same two shops and have done so over the 30 years I've been buying Harleys so maybe I'm just lucky. Even when I owned other brands I stopped by and stayed in touch with friends who worked there, went riding with them etc. I have had salesmen try to tack on the extras but I just say no untill they get the picture, I'm not afraid to point out that my money and credit work just as well elswhere. I guys buyer beware is the key.
The Harley Stigma is a fact of life as you pointed out, a lot of people find it off-putting, again it doesn't really bother me, I wear the same Arostitch suit whether I'm patched up on a function or just out knocking around catching some air. I guess realistically I do lean toward the pirate end of the scale with my chain drive wallet, black HD shirts and club braid on my key chain and handlebars. I'm a large bald guy with a beard, what else am I going to look like?
I guess the bottom line is that I don't like copies, I value authenticity and if that comes with a few negetivies I'd rather suffer them than feel like I was a wannabe. As I said I'm sure the Yamaha is a fine bike, most of them are, just not for me.