I bought a Road Glide Ultra this time as it is the best in handling of any of the Harley Baggers. It moves the fairing away and does not feel as confining as an E Glide. It is a signifigant improvement on windy days as well. I have owned 8 E Glides and have not one bad thing to say but the Road Glide Ultra has all the add ons I wanted and the lower fairings are vented and work well in the real world.
I would try a Road King an E Glide and a Road Glide. If you want a smaller bike than these the new Dyna Switch back works like a smaller Road King and is about 90 lbs lighter than a Road King. They are a new model for 2012 so there are not many used out there. Our dealer cant keep them in stock and has several sold by deposit for future delivery. My wife is 5ft 4 and can flat foot and she likes the lighter weight. I like the old school look.
As far as the Harley lifestyle it is what you make of it, I am any thing but a pirate , I ride nearly 20,000 miles a year and have ridden more than 40 years, I have ridden all over the world including Europe, Austrailia New Zealand and from Alaska to Mexico. I ride with stock pipes and wear ballistic nylon jackets and pants, I do enjoy socializing with other riders regardless of there choice of bikes, It is there money and they can spend it as they decide.
It seems the people who have the most trash to talk dont own or ride a Harley. I do see more people trying to turn the Metric bikes into Harleys by adding Harley style fairings and bags but they are never going to have a real Harley going that way. Again it is thier money , they earned it and can spend it as they want.
Find a bike you like and ride it with out worrying about others opinions.
I would rather be lost on my Harley than found at work...