1. Is there a model year that incorporated a step change in modifications that would make that, or later model years more attractive?
While I love my 04 and have experienced no problems, Triumph did beef up the tranny gearing by 08. There were some early casualties, and the company created an "update kit." Also some of the early ones had the output shaft bearing installed backwards. Or was that the oil seal? As far as I know 08 and on are the bikes updated in every way.
So it becomes a matter of preference and personal fit. For an older bike, footpegs and straighter bars are the Standard model. The classic added boards and more pulled back bars. And striping. The Tourer was a fitted out Classic. These models are no longer made, and you've got the Touring and Roadster to choose from.
The Roadster pegs are moved back almost 6 inches and down an inch or so from the Standard for more upright seating and foot position combo. The Touring is a different beast, with frame changes and narrower tires, supposedly handles really well but I haven't hardly seen another Rocket, never mind ridden one.
There are bikes that come up for sale here, and you can find beautiful well cared for machines all farkkled out for pretty good deals. Some strip off the add ons and sell that stuff separately. Good luck in your search, and welcome!
Oh, earlier bikes need a relay kit added on for the headlights, as originally the lights ran through the ignition switch. Many failures and strandings. That has been corrected by 2011, perhaps a recall of the 2010 model year? Eastern Beaver H4 headlight relay kit has been the overwhelming favorite, while some build their own kits, and others jump around the switch. This is a must have!
Make sure you check out T Evans ride in OK
06 Rocket III Classic - R3Owners Classifieds