This is a good discussion so far. I was looking at the Triumph Trophy's myself years ago as a replacement for my R100rt, but never did find the right deal on one. Ended up going with a Sportster and couldn't be happier. I like the Road King solution, or any of the Road King-esque copies. That type should be worthy of a good look. I'd suggest trying a Nomad before buying, if possible though. I worked on an early 1600 for a friend years ago, and he asked me to put a couple hundred miles on it to hopefully get an intermittent problem to show up. That was, hands down, the most uncomfortable bike I've ever ridden. May fit you like a glove though.