Sure the Nightster will open up on a much greater percentage basis than a Japanese or European bikes is because they are tuned so poorly from the factory to begin with. If I'm not mistaken your bike is a 1200cc bike that makes about 55 hp at the rear wheel. I'm sorry its 2009 and that is really pathetic. On a cc to hp ratio that is about the poorest I've ever seen, 50cc scooters are better, seriously. So yes if you chip it, and open up the exhaust it will run much better. Hell my 25 year old Yamaha Vision 550 made 57 hp way back in 1982, and it was a V Twin, and it didn't leak oil either.
As Fred said do I hate Harley, of course not, but do I think they are lost as a company, yes. They are the king of junk vehicle loans; think Franny and Freddie here. The loan default rate is huge and they may get into a death spiral. Now the new XR1200 shows that they do have at least one engineering team who gets it.
As far as getting older (I'm 44, does that sort of count?) and not buying a 1098S, actually if I could fit one in the budget I'd have one. For this year I'd like to get a dedicted track bike. If I was getting a larger touring bike it would never be a Harley, maybe an FJR or ST as I know both run great, are comfortable, reliable, handle well and are quick.
It is what it is...