I play in a keeper league and I need your help. It is AL ONLY, auction draft, and you can only keep TWELVE players from season to season. Two catchers, ten teams. We also need to roster a DH who has more than 20 games a year at DH, making guys like Montero more valuable than in a normal league.

After you’ve kept a guy for two years, you need to either extend him at $5/year for as many years as you want or announce that you will give him up after the following season
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Keeper inflation is about 30%. Pujols sold for $44 at auction last year, Darvish for $30, and middling players like Morales and Liriano for around $20. Guys who aren’t special but are guaranteed a starting job tend to be worth $14 or so. Auction budget is standard $260. Here are my certain keepers:

• Carlos Santana - $4, $9, $14, or $19 (Would have to give him up after 2013, 14, 15, 16 respectively)
• Jesus Montero - $10, $15, $20 (Would have to give him up after 2013, 14, 15)
• Will Middlebrooks - $4
• Mike Moustakas - - $4, $9, $14 (Would have to give him up after 2013, 14, 15)
• Jurickson Profar - $10 (But I’ll be able to use him as an expansion pick and get him VERY cheap through the next few years)
• Wil Myers - $4
• Mike Trout - $4
• Brett Anderson - $1
• Matt Moore - $4
• Brandon Morrow - $12

I also have a TON of borderline keepers:

• Mitch Moreland - $3 (Would have to give up after this season or give an extension to)
• Dustin Ackley - $4 (Needs extension)
• Luke Scott - $1
• Lorenzo Cain - $10 (Needs extension)
• Nolan Reimold - $4
• Dayan Viciedo - $10
• Felix Doubront - $10
• Erasmo Ramirez - $10
• Garrett Richards - $1
• Anibal Sanchez - $20
• Dan Straily - $10

So I can keep two of those guys in addition to the ten I am keeping for sure. Right now it would probably be either Cain or Reimold (depending on spring stats) and one of Doubront, Straily, and Ramirez (depending on spring stats).

Question #1: How long should I extend Santana, Montero, and Moustakas for? Right now, I’m leaning toward $14 Santana through 2015, $9 Moustakas through 2014, and $10 Montero whom I’d have to give up after this year.

Question #2: I’m being offered a trade. The deal is Scott, Ackley, Moreland, Viciedo, and Morrow for Robinson Cano. Cano would cost me $31 if I just kept him for this year or $36 if I wanted to keep him for this year and next as well. The only slam-dunk keeper I’d be losing in this trade is Morrow, but I have him for this year and next at $12. I’d also be losing several trade chips that are reasonably (but not very) valuable. Is this deal worth making? I would also be building my pitching staff even more from scratch at the draft, keeping only Moore and Anderson. I could go big on Verlander, who will be in the auction, but I’d be stuck with lesser names on the bottom of my staff.

I could also probably get Pujols at $44 or Fielder for $37 without having to give up anyone too significant. Would this be a better move?

Lots of stuff so I hope I cover it all.

If you don't do any trades, then I think I would keep Ackley and Anibal. I don't love either but the prices seem pretty reasonable and they give you the most production. Ackley is an easy keep in an AL only especially at that price.

This is based on the money you said guys usually go for. I would be inclined to extend all three guys to their max. I think Santana is a very good catcher and will be well worth owning even at $19 in 2016. Montero is only going to get better and with the fences being brought in plus a DH, no problem locking him up until 2015. Moustakas is a solid 3B with plenty of upside. He would be the only questionable one but with this being AL only, I think i would risk it and keep him til 2015 as well.

As for the trade, I can't really come up with a good reason not to do this deal. $31 and $36 seem like bargain if you compare them to what similar players are going for. He is better than Fielder but comes with a much friendly price tag. The only thing it hurts is you don't have the best group of keepers to sub Morrow with but I don't think I would let that get in my way. While money is always something to think about, I always want the best players and Cano is a top 15 player.