I just had this great debate with myself for the last few months. I settled on the 2013 CVO Road King With a Dragonfly. Here's my reasoning:
1. Riding is an escape for me. The stripped down cruiser style of the Road King opens up my sight lines to the road and gives me more an open feeling that helps me escape whatever it was I needed to get away from.
2. About 70% of my riding is short distance. While I acknowledge the fairing makes a substantial improvement on long hauls, it's extra weight when I'm running errands around town, etc.
3. The Dragonfly option gives me the fairing when I need it and the stripped down style when I don't... The best of both worlds.
4. The Dragonfly option with the Zumo 665 gives me both GPS and XM radio. Combined with the iPod on the FLHRSE5, I have all the audio options I would use... (FM radio is not needed for me)
5. I live in Texas... We don't have a long harsh winter. I can ride comfortably behind a windshield nearly year round.
I admit... There is a trade off... I came VERY close to buying a 2015 CVO Steet Glide. The Ultraviolet/Lava paint job on that bike is just a beautiful work of art. Also, the upgraded audio will outperform anything I can easily put into my Dragonfly.
But, for me, it came down to "good enough" audio, and the flexibility to build up my bike from a stripped down Road King, to a "Street King" with the Dargonfly, to a "Street King Ultra" with a Tour Pak, and then to strip it all back down again. Ultimate flexibility and enough creature comforts that I shouldn't complain for many years to come.