The way I see it, if you are only going to have one motorcycle, it should be Japanese, or any Harley but the Street series. The quality and reliability of Japanese and traditional Harleys is WAY above the Enfield and Harley Street series. If you have a high quality, reliable bike that you can depend on when you actually need to take a long trip, or commute back and forth to school or work, and are interested in a bike more for pleasure than anything else, and can deal with a few things going wrong, then an Enfield it the bike to get. The Harley Street series is probably less reliable than the Enfield (Yes, I have actually ridden one) but provides none of the Enfield's looks or character, and would not be easy to work on. I can sort of see it for the Indian market, where price is a big deal, but I have no idea what it is doing in the U.S. I can buy a like new used Sportster 883 for less, and it has real Harley looks and character.