I am struggling with the same question right now.
Softail gives you that great feel of being part of the bike
Touring gives you the comforts to enjoy the bike for longer periods of time.
I really would like to make my deluxe a convertible but to get the hard bags i like and the nice fairing i would like that would run me close 4.5K to do it right so i am trying to work a deal for a '10 street glide

 

Most of the guys I run with ride SE Electra Glides or Street Glides because here in Florida a short ride is 150 to 200 miles and they handle like a dream. Check out "Ride Like A Pro". Even though I ride the SG 3 times as much as my FB, I'll always own a softail cause its pure fun to ride. I'm lucky, I own two bikes but if I could only own one it would be the SG.

 

For your type of riding, I would own a touring bike...

 

If I could I would own one of each, I have toured cross country on the Fatboy several times, it can be done.

In my experience the SG is more fun to ride, but I'd rather be seen on the Fatboy.

 

owned a 2009 Roadglide for a month, sold it and bought an older carbed heritage. I love this bike, best HD i've owned so far.

RG was nice on very long rides but most of my miles are in town to and from work and weekend trips/poker runs/bar hoping