If it were me . . . 1st choice would be the Switchback, then a FatBob.
After owning an 02 Electra Glide (for a short time), I want a fairing. The
Batwing is great!!

So either one of those models.
A yr or so ago, I saw a black Switchback with a Memphis Shades fairing.
Looked sweet. like it belonged there. So that or a Woody's. I'm on the fence about a radio.

I'd like to ride one (again) with the vibration issue resolved.

Very nice handling, lightweight.

 

I'm biased to a FXDX/FXDX-T. Preferably the T-sport over the DX for the adjustable suspension. The problem with that is finding one that does not have sky-high miles on it and what kind of abuse it endured. Can't go wrong with a used Streetbob.

 

You know the old saying about opinions, everyone's got one.
So here's mine. I ride with 4 friends literally almost daily. Between us, there is a 14 Fat Bob, 16 Street Bob, 17 lowrider S, 13 48' and a 14 wideglide.

I have ridden each one extensively.
IMHO, by far the Fat Bob is the most comfortable, holds the road best, and handles the best.
I could go into all the reasons why I feel these things, but I will say between my group it is unanimous about the comfort.

In short, try and ride them all, then you decide which one you like.

 

Test ride them all. No one can decide for you. If i wasn't so picky, a 2014+ low rider would be it for me.

I know you want older but, i can't really see any sense in that. Might be better to find a style you like then hunt for the best deal rather than limiting yourself to a certain year range.

 

I'm biased towards the Superglide Custom because I have one and am selling it
But seriously its a great bike that has plenty of power and such a versatile base to start customizing.