I wouldn't get caught up in the 100th anniversary hype, unless that is really your thing. I would recommend starting on a used bike that weighs considerably less that even a Harley Sportster. This really helps with the dropped in the parking lot while I was barely moving factor. If you just have to have a Harley a lot of Harley riders start out on sportsters and then move up, so you should be able to get one used in good condition.