Is there any particular game that you really regretted that you bought brand new?
For me, I would say I regretted buying Kameo brand new. Don't get me wrong, the game isn't bad. It is just not $60 good.
Two games come to mind that I really regret buying new. The first is "Leisure Suit Larry: Box Office Bust". Even at $20, it was the biggest waste of time since "Sneak King"!
I regret buying Call of Duty Modern Warfare 3 and Halo 4 for their full price at release. It was a total waste of 60$. I really wished that I didn't go impulse buying and instead have waited for both games to go on sale for a much cheaper price. Honestly it's never worth it anymore to buy new games at a full retail price of 60$. Your wallet goes empty very fast.