I know exactly what you mean - my other bike is a 1999 Indian Chief my brother purchased new. A couple of weeks ago when I saw the Craigslist ad minutes after he posted it, I jumped in my truck, drove the hour and a half there and started laughing when I saw it - then I immediately stopped when the guy came outside because he really took so much pride in it with his limited finances.
I've had it almost two weeks and have been riding the hell out of it, but I do wear a dark visor so I can be incognito. thnx!