Pull the trigger on the FXRS. You wont be sorry.
And then go out and eat us guys with newer bikes alive.
And watch us wish we had something like yours

 

Here's the thing, most people mod the crap out of their scoots over time. You have a set budget so, just find a bike you think you can make your own over time and in your price range and don't think of it as the final picture.

With some TLC a Hog will last for eons; a bud of mine rides a '40 something and its still going strong so I'd forget the age unless it looks and runs like a piece of junk.

Sportsters are cheap to mod but unless you are pretty slightly built you'll probably regret your purchase as its just a small scoot. I'm 6' even and honestly prefer the looks of the stock Nightster to my Street Bob but, I'm too big for it so I got the Bob... See where I'm going with this?

Just pick a bike you can ride comfortably and make her your own

 

in 2005 I bought my FXD. I put 2K down and got my note at $240 a month. Since then I've been able to do some customizing. IMO, put the 5k down on a SG. The sporty is a little small and an older bike is nice to have,but a new bike has no worries. Fire up and ride.

 

I think ill save some more up then and just try and find one cheap in the offseason, but dont know how long I can wait, already been waiting 2 years but quess one more summer wont hurt