I can throw my 2 cents in:
1) there is definitely a mystique riding an HD. I rode a Softtail Deluxe for a while. Have gotten way more compliments on my LT than I ever got on the HD. Great cruiser, cool to ride, comfy, stock exhaust isn't too loud, very pretty bike... I just wouldn't want to purchase HD for $25k, add $10k worth of chrome and accessories that should just come standard for $25k, plus repairs/service. With LT, or any Beamer for that matter, you get the bike with everything you want, plus access to forums like this and the great people out there who love riding. Not people that ride with ridiculous exhaust, revving past grocery stores, dressed in orange, and "ride to live" but really just "ride because I have a Harley and you don't, so my shlong must be bigger."
2) the only reason I feel bad for not buying an HD is because I live in Milwaukee (both Mil & Madison). HD is huge here. If you drive through Detroit, you see nothing but Ford and GM - same goes for HD in Wisconsin. HD is Milwaukee is why Wisc will never pass a helmet law, but that's another subject. I didn't let living in America keep me from buying a European car. Same goes for my LT.
3) this IS a BMW forum, so the convert population is probably pretty high. Has anyone ever realized that people rarely convert from a Wing or LT TO an HD? I have yet to meet a person that wasn't completely satisfied with their Honda or BMW. Yet, talking to some HD owners, I've gotten mixed reactions.
The only way I would look into converting to a full dress HD someday is if I had the money. Then again, why leave BMW when they make a superior bike? I guess it all depends on personal preference. People are happy with and passionate about whatever bike they choose. We here on bmwlt.com just inform that falling in love with a BMW won't be as hard on your wallet and tolerance for repairs in the future... and your ears and back muscles.
Sorry for the epic novel of a post. I'm just convinced that HD isn't the bike to get. IMO, I feel such libel & slander is like blasphemy since I live in Milwaukee.