I bought my first machine in late 2006. Between then and about 2012 were some good deals. It seems like 2012 was the turning point where most of the really good deals dried up.
My biggest highlights:
2007:
ST:TNG $2,000
Blackout $300
Judge Dredd $1,000
2008:
Cirqus Voltaire $2800 + JD ($3800 total)
High Speed $350
2009:
Wheel of Fortune ("NIB" but used at a show) $2350
2010:
Judge Dredd (sample/early machine and nicer than my first) $800 (wish I still had this one...)
2011:
Whirlwind Diamondplate $1600
2012:
Demo Man $1200
Would love for these prices to be normal again!