But Amaro re-signed Rollins after 2011 while also adding Papelbon (and Jim Thome!). Then, in 2012, he picked up Ruiz's option and signed Mike Adams and John Lannan (yikes!). And then in 2013, even after dumping Vic and Pence and firing Charlie, they still extended Utley and kept trying to win on 2014 (Marlon Byrd, AJ Burnett). And of course they were already stuck with Howard.
The turning point for moves like the above is coming up, but it hasn't come yet, and the current core is miles better than what the Phillies had in 2012. In the meantime I don't see how you really think they could productively move on from the players you might want to (Casty, Turner, Walker) in a way that makes the team better short or long-term. Ditto Schwarber and JT who are both essential this year and not otherwise an albatross beyond that if you don't want them to be.
Middleton was the guy who pushed for them to sign AJ Burnett (to make up for the Lee and Halladay declines), we'll see what lesson he took from that era. Certainly they wouldn't have traded Pence just to get under the tax under his ownership.