My Evo Dyna Wide Glide was fun at slow speeds. It felt good, sounded good, and looked great!
Sounds like you really liked that bike. If you think a bike needs to be heard from 8 blocks away, you are going to hate the Strom. As for the looks, I actually really like how the Strom looks, but you can't see much of it while riding, I don't like coffee so what it looks like at the curb at Starbucks doesn't mean a whole lot to me.
Is this bike fun to ride when you're not in a hurry(obeying speed limits), and the scenery is somewhat bland, and the road is mostly straight, and you've been in the saddle for a while?
I'm not sure why I would want a bike if I'm obeying speed limits...
Seriously though, that kind of drive, I'd rather be in my truck, set the cruise, Sirius sat radio, cold drinks, take my shoes off, etc.
Does the Wee/Vee have enough character to keep the ride interesting all on its own merit?
Well, I mainly commute on mine, but almost everytime I get off of it I say to myself "Damn, but I love that bike!"
Do you look back at it when you head in from the parking lot, or look at it from inside the window eagerly awaiting your time to ride? Does is MOVE you? Did you name/nickname your Strom?
When I ride it to work, I'm constantly going to the window to look at my Wee. When my wife and kids first saw it, they said it looked like a Japanese beetle from the front. Mine is also orange, I call it Beetlejuice!
I'm not sure what you are looking for, but I came to the Wee from a cruiser. It happened to be a Suzuki Intruder 800 and not a HD.
I wanted something more comfortable, with better wind protection (you are really exposed to just about everything on an Intruder), no chrome and no spokes. I wanted to sit more upright and not have my spine vibrated to death. I absolutely dreded riding my Intruder on the highways.
I've got all that and more with the Wee. Took me a bit to get there, I started looking at other cruisers. Thought my ultimate bike was a M109R, it was out of my price range, but rode a M50, more comfortable than my Intruder, but I didn't like the bar position, and still ultimately my feet were out in front. The Wee ended up being the perfect bike for me so far. Great commuter, much more responsive than my old bike, no chrome to polish, no spokes to clean. Hell, I haven't even washed the thing since I got it in August. Upright riding position and no killer lower back pain that evening after a couple of hours riding. I can also see taking extended trips on my Wee that I just never could see doing and not regretting it on my Intruder.
Maybe you should list the reasons you feel you need to move on, because all the questions you did ask scream for another HD.