I had a 90 model Heritage Softail Classic prior to the Roadie. The Harley was a good scoot but I got tired of having to tighten things up every week or two. The Evo motor is a good motor, but underpowered compared to the Roadstar. I've put 41,000 miles on my 05 since I bought it & it's dead reliable. Comparing cost the Road star wins hands down. We do at least 2 or 3 long distance trips a year & I ride daily to work. Lots of extras you can add to both, so no real difference there. Also the Roadie feels bigger & is much smoother at highway speed. Winner all around in my opinion is the Road star, especially at prices about 40 to 60 percent of what you'd have to pay for a Harley. Enjoy & welcome to the Forum!!!