Harleys and Mopars have a lot in common, you generally either love them or hate them. I have had a Harley in the garage for many years (not the same one). I have had iron head sportsters, a flathead, a 78 Shovel and a couple of Evo's and I currently have that same 78 Shovel and 2 Evos. While the idea of having an old harley is appealing, the reality of it isn't unless you are just in love with them and working on them. I used to equate riding my shovel to flying a Helicopter; 2 hours of work for every hour of riding (not really but is seemed like it). I love the shovel as it was the first HD I ever actually liked (saw one new in 78); however I have chopped mine now and it has a rigid frame springer front end, etc. I keep it to look at and ride the Heritage and Ultra.
Like Mopars, Harleys are more of a "way of life" in that its something you should do because you love it, not because someone else thinks you should have one. Modern bikes (all brands) have come a long way from the old bikes and are relatively trouble free and fun to ride. Yes there is something nostalgic and cool about an old Harley but unless this is your passion, get something that speaks to and more importantly fits you, don't worry about the name on the tank.
Completely agree that you need to learn to ride on something other than an old Harley. You need to focus on learning to ride rather than keeping it running not to mention the 30lb clutch cable. You can pick up an older street bike off your local craigslist for cheap and beat the crap out of it, plus that experience will really tell you if riding a MC is something you even want to do.
