First up, a 2008 isn't a Roadster; it will be either a Standard (came out with pegs, solid colour, twin seats) or a Classic (boards, 2 tone, pull back bars, dual seat). The Roadster wasn't released until 2010, presumably while Triumph mulled over the colour scheme, with claimed increase in power (but not really borne out in fact), ABS and the pegs moved back and down - stupid move in my book.
'08 and '09 models are arguably the best because they did indeed have pretty much all the bugs ironed, a more sensible and comfortable (to me) seating position, 3 pipes instead of 2 enormous goofy feet and at least some choice of colour. I wouldn't mind the ABS though.
All Roadsters are black (yawn) and the biggest change on the latest one is the exciting and bold addition of even more black. They've also removed the power restriction in the first 3 gears that most of us simply removed on earlier models anyway, but have the drawback of having a locked ECU preventing further tuning enhancements.
I ride my '09 every day and it's given me pretty much no trouble beyond what you'd expect from 55,000km.
Welcome to the site. Stop thinking; just do it. Whatever model you buy you will love it.