I regret buying my PS3 when I did back in 2007. Should've waited two more years before buying one. I was mainly playing PS2 games and Warhawk for a year and a half. Pretty much every game I was interested in was a disappointment to me. I enjoyed Ratchet and Uncharted, but they didn't keep me coming back.
Also regret buying a PSP - bought it for God of War and Crisis Core. God of War was okay, but it had no replay value. Good thing I rented it. Crisis Core was terrible: terrible dialogue, easy yet crappy gameplay, etc. After that, there was a huge drought. Nothing else good came out on that year. I enjoyed Final Fantasy Tactics and Jeanne D'Arc, but that's about it. I sold it for a DS. Hate to say it, but Sony disappointed me this gen.
Other regrets: MGS4, Star Ocean IV, Knights in the Nightmare, Super Robot Taisen: Endless Frontier, Demon's Souls.
