No Harley anymore but for years I rode a 1990 FLHTC (Electra Glide Classic). I rode it until I had about 60,000 miles on it and traded it even up for an almost new (170 miles) 2000 Ducati Monster with a V-Twin 904cc engine. That bike was a lot like the Buells that Harley sells in some of their dealerships. I have since sold the "Duc" and am currently bikeless.
2) What do I like about the: a) Harley is the amount of storage I had. The bike comes equipped with a Tour Pack (trunk) which has integral backseat armrests and HUGE hard saddlebags. The bike was amazingly comfortable on long rides, like sitting in a La-Z-Boy. The upright seating position creates an impact problem for the lower mandible if you hit a big bump or a pothole.
b) Ducati, 65 mpg, a 4.2 gallon tank and a six speed tranny = 240 miles before I even hit reserve! The Duc was also THE fastest scoot I ever rode although it was not a crotch rocket, per se. It was what Kawasaki calls a "naked" bike. Not quite upright seating like the HD but not bent over in a Kamikaze crouch, either. For the type of bike it was it, also, was pretty comfortable. The speed came in handy when a "buy American" redneck decided to tailgate me once because I wasn't on a Harley or a Victory. He became a dot in my mirror in about 2.5 seconds. With the V-Twin this bike sounds as cool as any Hog.
3)What I didn't like about a) the Harley was about 40 mpg on the highway. Plus, in crosswinds that thing was like a sailboat. For example, during one of my Sturgis trips I made the mistake of taking 90-94 west from Illinois instead of taking secondaries like I normally did. When I crossed over from Minnesota to South Dakota the crosswinds started and there were a few times I nearly became "semi chow" or went into the ditch. This is the reason I have heard that some people hate the solid wheels on the Fat Boy. b) The Duc doesn't come with hard bags and soft bags have a tendency to get caught between the composite fender/rock guard that is about a half inch from the tire and the actual fender upon which the seat/taillight is mounted. So not a lot of storage on the stock version and the hard bags are muy expensivo. Also, not a lot of mechanics out there for the pizza burners.
4) If I could go back to the day I bought my "geezer glide" I would have bought the Buell with an 883 and had it fitted with hard bags and lowers and maybe a trunk for long trips. For a bike that weighs in about 450 dry the 883 is plenty. Either that or I would buy a kinda tricked out 883 Sportster with straight bars and a single seat and had the hard bags and a bullet fairing put on that. Bigger tank, too. You would get about the same effect. I don't remember who it was in this forum that had a Sporty that was set up kinda like that but it was way cool. It also looked like it would fit a tall guy like me pretty well.
Now, I know in advance that what I am about to say is real sacrilege and I will apologize in advance to any HD riders that I offend and I know that I am a bad person BUT, one of the big selling points of Harley has always been individuality. You can buy the HD and spend 5 or 6 grand tweaking it until it looks like you and in the end it is still a Harley. In Sturgis, about 70% of the bikes I saw were Milwaukee Muscle. Aside from cosmetic changes, chrome, and custom exhaust what you have is a Harley. In all the years I went to Sturgis I only saw one other Duc.
Now that, mi amigos, is an individual.