The Sportster is a fun bike for around town, maybe up to 25 or 50 miles, but the vibration of a solid mounted engine, even with iso-grips and pegs can wear you down. This winter I decided to go long on the ol' loan dept, and picked up an '07 Electra Glide Ultra Classic, or as it was desribed in American Iron magazine, the Party Barge.
This is the one with all the bells and whistles-- AM/FM/CD/CB/Intercom audio system, cruise control (this is pretty funky), security system, etc... The seats are seriously sofa class. Kathy loves the back seat. After having a used bike for 4 years, and constantly doing tweaks and fixes, I decided to keep this one fairly stock (not that I can afford any customization on it right now). As a buddy put it, buy it, break it in, and ride it like you stole it.
I did do two changes, first was a taller windshield. The original was at a perfect height if you were 5'2", or 6' 8", but in betweeen (I'm 5'11"), the top of the windshield cuts right across my field of vision. Useless! I went with the taller windshield, at least for the winter, and it is really nice. My only gripe is that it's shaped sort of like a mushroom, bulging out on the sides... Hey Harley, how about some style here, straight sides would be much more slick looking. Oh, well, not a problem. The other change was to move the rear passenger pegs up to the top notch. The middle setting put my wifes legs against the rear bag guards, and was uncomfortable for long trips (or even some short ones).
If I do anything else, it will probably be putting on Kuryakyn Isogrips, and different slip-on. Maybe do the 103" upgrade next year when the winter prices come down. Here's some pix of the party barge, and my wifes 650 v-star.