Ironheads are getting old. The chances of finding one that runs good and hasn't been ruined are getting slim. Most of them are in pieces or tucked away in the corner of the garage, unridden, neglected, and slowly dryrotting. If you get one you will work on it more than you will ride it. A lot more. You will also put more money into it than you will in a newer Sporty. They are about the same price. I've seen fantastic deals on used EVOs. Get one and enjoy it. I have more money in this little lady than you want to know:

 

I had a '72 XLCH in 1976 and then a '79 XLS in '79. Both bikes were trouble free and I rode the **** out of them. Maintenance consisted of oil changes every 1000 miles and occational vavle adjustments.

That being said, I would still recommend buying the newest bike you can afford. Not just for quality but for efficiency. An evo motor just works better than an ironhead. Hard to beat the looks of an ironhead though.

 

Still the best looking Sporty's tho

 

My first street bike was a '72 XLCH bought new. I never had any problems with it except that one time I holed a piston racing a honda 750... how embarassing. I did have to push start it quite a bit in the cold mornings. And things used to fall off of it every once in awhile, but I didn't really know about locktite back then. It's the only one of my previous bikes that I wish I still had...

 

Shout out to carlgrover, thats a SWEET lookin' bike.