Few teams are worse than Juve at keeping possession. Siena are doing equally well in that department. We live solely off the brilliance of certain individuals.
Del Piero should be doing a lot more to make us keep possession, he's capable of it. Also an experienced player like Sali shouldn't give the ball away so easily. Diego substitution in this situation is really strange, I'd understand Giovinco or Camo, but not Trez.
Because our midfielders are incapable of it. It has nothing to do with system, just Melo, Brazzo and Momo aren't particularly known for their intelligence with ball.