Craig-
I think that your local HD Boutique is a bit optimistic w/ that price. Especially 'chopped'...Still "rare years" & "prime original examples" are getting $15,000.- $20,000. on fleebay. (I have seen this)
Actually I like all old HD's, But I am currently also enjoying my recently finished Police Servi-car, Rare year only 425 made.
Of course I did modify the motor a bit.

I Bored & Stroked it out, & am running Leineweber cams, & about 59.4 other internal mods.. ;D To increase the 'fun factor'....
I'm digging it.... 'G' 45 's are for Servi's, WL= solo's
My first HD, 35 years ago was a '47 chopped servi. No rake, looked like it was going uphill. ;D
That was a fun 'Parts Chaser" This current one is my 2nd Servi, & a fine 'Parts Chaser' & then some !! This one looks "stock" = aka 'sleeper'

As far as values, I see the old Iron increasing in value, no matter what HD it is...But parts availability is there.
Sometimes you may have to look a little harder.....