Never pay premium price for non elite pitchers in their 30's.
Pitching is always risky by nature, and the only way to mitigate the risk is to stick to guys putting up elite results over an extended sample, who have a chance at aging gracefully (aren't completely reliant on velo). I don't know if Ray qualifies there.
I remember after Martin threw the ball that ricocheted off of Choo's bat just thinking no, absolutely not, the season is not going to end like this. Then Bautista did that. Best moment of Jays baseball in over 20 years.