Let's talk... Ironhead Sportsters

A local car buddy of mine is also really into bikes; his dad was a real-deal biker "back in the day" and has a crazy built Shovelhead that pulls wheelies. My friend showed me that bike as well as his 1947 Knucklehead and needless to say I really want an old Harley now. He recommended I go with a Sportster because I'm 6' tall but only 150 lbs lol. Now I'm trying to find what info I can on the old Ironhead models as it seems the Evos are obviously much more popular nowadays. So what's up with people complaining about the maintenance? Tuning a carb, ignition timing, valve lash seems like easy stuff? I get the idea that most riders aren't necessarily mechanically inclined which leads me to believe if I could teach myself how to build car engines I can probably teach myself how to work on an old motorcycle.

Also regarding safety, yes it would be my first bike and YES I will be taking the rider safety course most definitely.

Any advice, stories, etc. would be greatly appreciated!