Roadster or Touring just depends on which style you like. The Roadster pegs are more in a 'standard' position. The frames are really different and they ride very different. The Touring comes with much less power, but that can be changed with a few mods. Tires are probably the biggest expense on the Roadster. Tires on the touring are smaller with a wider variety available.
Mine is an '04 Rocket III Standard. The Standard evolved into the Roadster a couple of years ago. It currently has 71K+ miles on it and runs great. Mechanically, it has been pretty much bullet proof. My biggest gripes are the Primary Throttle Position sensor, I am on my 3rd one, and dealer service support. Triumph dealers with a competent service department seemt to be few and far between, however, the Florida guys on here usually have good things to say about their dealers.