I would personaly not be confident enough to get the breakout shape, so I would play safe. As RiverCity said, don't wait until you are looking at the tied up balls to play safe, play safe NOW and keep playing safe until you see the out. If you wait to play safe against a better player, you are just cutting the weeds for them, making it easier for them to win.
I had a very similar hill-hill situation recently against a very straight shooter who has no clue about strategy. Because I knew my player, I ran to the 7 (the 8&9 were the ones tied up), and shot it pocket speed to just miss, leaving him straight in. Of course I had to act like I was mad that I missed the easy shot. He fell for it and made the seven that had no hope of a breakout, and then was forced to break out the 8&9 to leave me a two ball out. He still thinks that because he is a better shooter, that I beat him every time out of luck. Keep in mind though, I would only play it like that against someone who I know can't play safes as well as me, or someone who knows nothing about strategy. If they know some basic strategy, I would play the first good safe I see.