Let's talk... Ironhead Sportsters
New Harleys are very dependable, I bought my 06 Heritage new and beside changing the oil have never done anything to it. Manufacturing techniques have become so much better than in years past that its uncommon to really find a dud; don't get me wrong there are lemons in every brand and every model but its more of the exception than the rule.
As to a motorcycle, if you like them and want one, get one that really speaks to you and that you really want than what others think you should have. Die hard Harley guys re just like die hard Mopar guys; they believe in their hearts that this is the only brand that should sold and used and there is nothing wrong with that until it becomes an emotional issue. I love Harley's and I love Mopars but fully understand that there are brands other than these in their respective categories that are good and are loved by someone. Likewise, I have owned other brands of both cars and motorcycles, but I choose to focus on these two. If you like the look of a Harley, go and visit a dealer, while you are at it, look at Indian and the other brands; you will know when you have found "the one".