Coco says he wants a longer term deal, Beane has said picking up his option is a no-brainer. Any thoughts on the A's getting Coco for more than a year?
Crisp's current contract has a $7.5M club option that is all but certain to be picked up. Indeed, given his level of production last year and (relative) health, it will probably be a bargain.
An extension from that, however - at least this year - seems unlikely. Historically, the A's are not big on extending players who are into their free agent years. In fact, I cannot remember the last time the A's extended a player they had acquired in free agency. Even a guy like Bartolo Colon, who even at 40 years old is a decent bet to have a league average pitching line next season and who the team retained control over the entire year was not offered an extension during the season. The players in recent memory who were signed to extensions even, Trevor Cahill and Kurt Suzuki, both found themselves shipped out in relatively short order. That said, with Cahill, in retrospect, it is pretty clear the A's signed him to a reasonable deal with an eye towards being able to leverage that cost control in a future trade.
Whether it is a prudent deal to make with respect to re-signing Crisp as far as his numbers are concerned is also largely dependent on how he performs in 2014. He hit a career-high 22 HRs last year, but his 21 stolen bases dropped off dramatically from 39 in 2012 and 49 in 2011. His game is evolving as he loses some quickness (though still a stolen base threat and an excellent baserunner in general), and it remains to be seen how his numbers follow. All that said, Crisp's current contract is a bargain for the 6.5 wins he has brought over the life of it. Indeed, Crisp is somewhat of a perennially underrated player, whose early-career penchant for injuries has stuck with him since. It's not without merit, of course, as he only played in 131 games last year and his 136 in 2011 are a high for him with the A's. Given that, any Crisp extension would price in his injury risk.
Do the A's trade away Milone/Griffin/Anderson/Straily to bring in another offensive weapon if they sign Scott Kazmir? Their depth at starting pitching is incredible, but none are the absolute number 1's except Parker/Gray/Colon.
I don't see any way that the A's trade one of their younger starters for an offensive weapon. In general, it is unclear what kind of value each starter actually has as part of a package to bring in a youthful offensive player. More than that, even, is as the A's are constructed, the only upgrades that may make a meaningful impact are big upgrades. Big upgrades mean trading away a lot of talent, so potentially two of the starters listed there That's why I think Scott Kazmir makes sense, because he has number two starter potential.
Addressing each starter in the sequence you listed, it is unclear what kind of value Milone has. There is a decent case to be made that he is significantly helped by the Coliseum's vast expanse; indeed, he has even said that he feels more confident pitching at home. The same could be said for Griffin, and he has shown a penchant for giving up home runs. Anderson is of questionable health, and may ultimately be a late-inning reliever down the road. What's more, when it comes to Anderson, he is at the nadir of his value right now, even with two club options remaining. Finally, for Straily, his value is up in the air. He has a minor league pedigree for strikeouts, but doesn't have the kind of major league success would be needed to truly make trading him worthwhile.
Does Scott Sizemore contribute at 2nd base in 2014? If so, where does that leave Callaspo/Sogard/(and potentially Jemile Weeks and Nakajima...)?
As much as I like Sizemore, I think he is the odd guy this winter and likely ends up non-tendered. Between Sogard, Callaspo (if he stays), and Weeks and Nakajima, the A's have several 2B options that will slot in either Oakland or Sacramento.
Does the A's pick up Chris Young's option, or drop it and make Choice the 4th/5th outfielder on the depth chart? Obviously Smith would be up there on the DH/outfielder as well.
There is about the same chance of the A's picking up Chris Young's option as the Cardinals winning the World Series in six games. It seems clear Michael Choice will be given every opportunity to take that 4th/5th outfielder role.
What happens to John Jaso with the presence of Suzuki, the rise of Vogt, and Norris? Trade-city for new prospects...?
Jaso is a much better offensive player than any of the other options listed. If he doesn't catch, he should DH or (learn to) play 1B depending on that day's matchups. He's a poorer man's Mike Napoli, but a little worse and better hair. Given what we heard about his progress during the ALDS, it appears he will also have recovered from his concussion by Spring Training.
Vogt did showcase himself well, so it's not hard to see him being packaged away for some younger talent, albeit someone very raw, low-level, or both. Otherwise, I would expect him to start at AAA as insurance for a Norris or Jaso injury. It is hard to see how Kurt Suzuki fits in. The A's will almost certainly decline his $8.5M option and pay him the buyout, and he will likely depart via free agency.