So, are you thinking of guns that will be more collectible (limited number made, special editions, no longer produced -- something you stick in the safe and never take to the range),
or classic in the sense it is unique in some way (Ruger 10/22 is "the classic" .22 rifle), but not necessarily going to bring many times its purchase price in 10 years?
As far as the 1911's you are looking at, what models & prices do you perceive as "damn expensive?" Case in point, OGC advertised two new SPRINGFIELD FBI PROFESSIONALS with sequential serial numbers for $2900 each.
Just curious what your thresholds for price and characteristics are when evaluating what constitutes a "classic."