I started collecting pins in I think 2008 or 2009. Thanks to the prices back then I've been able to sell those original games for a good profit and then roll that into future purchases. Below are a few of the games I remember buying back then and their prices.
Getaway: $1100 (my first pin, sold it a couple years later for $1400 and was very happy at the time to make $300...wish I still had it)
Twilight Zone: $2800
F14 Tomcat: $600
STTNG: $1400
Lord of the Rings (routed): $3100
Lord of the Rings (HUO, sold one above): $3500