Re: Would you sign Choo if given a chance
It isn't just about Choo, it is about the entire team. Bailey becomes a free agent after the 2014 season and then Latos becomes one after the 2015 season, and guess what 2016 is when Joey Votto starts becoming real expensive at 20 mil per year with Brandon Phillips getting 13 million in 2016 as well.
Consider that Cueto will need to be re-signed in 2016 as well, and right now he has a ridiculously team friendly contract, and there is simply no way you can keep the core of the team together if you sign Choo long term.
The reality is while it sounds good to say "Sign Choo", practically speaking it doesn't make a ton of sense. You can only be paying mid 30's guys so much money and Votto/Phillips are eating that up right now, paying Choo another 17 mil at 35 with the 32 already committed to those two, PLUS the huge raises due to the top of your rotation at the same time is how you hamstring a payroll/roster.
This is why you have a farm system. You can't re-sign everyone long term. As it is they can likely only sign 2 of the Bailey/Cueto/Latos trio long term, and not sure if you have looked, Mike Leake is becoming a solid No. 3 starter, and look how much those guys make in free agency as well.
Sometimes you have to let guys go, take the draft pick, and say "next man up". With Choo that means Billy Hamilton, when Ludwick comes up maybe that means Jesse Winker or Donald Lutz or whoever it might be. That is just how baseball works, can't play fantasy ball and just re-sign every guy looking short term without considering the long term.