Keeper advice in my big $ league

[Scott (Boston Padres)]

Hey all,
I emailed this too but some guys might be on the board more than email. Wanted to reel in some other opinions as I need to declare my keepers by next Monday in another league. My friends and I have run this league since 2000 and we're still going strong. It's 10 teams, 32-man roster, 5x5 and we do both Roto and Head-2-Head and split our pot - half for Roto and half for H2H. I'm coming off a Roto championship in 2014. We're allowed to keep up to 12 players and we have contracts that are 1, 2, or 3 years long which we can designate on a player the year after he's drafted. The round drafted (or month picked up in-season) determines the keeper value slot. With current contracts and guys who I know I need to keep, I'm pretty sure about 9 of my 12. It's the other 3 that I'd love to get some opinions on.

Here's what I'm looking at.
1st thru 5th rounds - I have picks in these rounds and would then have picks in any other rounds where a keeper isn't slotted or I've traded the pick.
6th round - Jordan Zimmermann, under contract for 1 more year
8th round - Kyle Seager, can keep here for 2 years, or would be a 7th rounder for 3 years, or a 9th rounder for 1 year.
10th round pick traded
11th round I have two picks
15th round - Byron Buxton, can keep here for 2 years or would be a 14th rounder for 3 years, or 16th rounder for only 1 year.
17th round - Michael Wacha, under contract for 1 more year
19th round pick traded
20th round - Garrett Richards, can keep here for 2 years or would be a 21st rounder for only 1 year.
22nd round - Jose Fernandez, under contract for 2 more years. I'll be able to move him to our 1 DL spot once the season begins
27th round - Hisashi Iwakuma, under contract for 1 more year
28th round - Kris Bryant, can keep here for 3 years or would be a 29th rounder for 2 years, or 30th rounder for 1 year
30th round - Yasiel Puig, under contract for 2 more years

My other players who I'm considering keeping. If I stick with the 9 above then I can only keep 3 of the following guys:
Ryan Braun - drafted 1st round last year, can only be kept for 1 more year as my 1st rounder.
Ian Desmond - drafted 3rd round, would be 3rd rounder for 1 year, 2nd rounder for 2 years, or my 1st rounder if I want to keep for 3 more years.
Buster Posey - drafted 5th round, would be 5th rounder for 1 year, 4th rounder for 2 years, or my 3rd rounder if I want to keep for 3 more years.
Yasmany Tomas - picked up in September and would be a 6th round keeper for 1 year, slotted up to 5th round for 2 years, or 4th round for 3 years.
Justin Morneau - acquired in a trade, was drafted in 31st round last year, would be 31st rounder for 1 year, 30th rounder for 2 years, or 29th rounder for 3 years. We do have a "collide" rule so if I kept him for 2 years as a 30th rounder, he'd "collide" down to slot into my 31st because Puig already has the 30th round spot.
Danny Santana - picked up in June and would be a 15th round keeper for 1 year, slotted up to 14th round for 2 years, or 13th round for 3 years
Lucas Duda - picked up in July and would be a 12th round keeper for 1 year or an 11th rounder for 2 years. Can't keep for 3 years because I don't have a 10th round spot to slot him into.
Cody Allen - picked up in March and would be a 24th round keeper for 1 year, 23rd round keeper for 2 years, or 22nd rounder for 3 years.
Sean Doolittle - picked up in May and would be an 18th round keeper for 1 year, 17th rounder for 2 years, or 16th rounder for 3 years
Matt Shoemaker - picked up in August and would be a 9th round keeper for 1 year, 8th rounder for 2 years, or 7th rounder for 3 years
Alfredo Simon - picked up in April and would be a 21st rounder for 1 year or 20th rounder for 2 years. Can't keep for 3 years as I traded my 19th round pick.

Let me know what you think. If you agree with my first 9 or not, and who of the other potentials should I consider. By the way, if I don't keep a player already under contract (i.e. Wacha, Fernandez, Iwakuma, Puig, Zimmermann) then I would lose that round's pick during the draft. So if I don't keep Wacha for 2015 then I lose my 17th round pick.

Any thoughts are welcomed and appreciated. Thanks!
Scott

[Chuck (Philadelphia Astros)]

I would keep Puig, Bryant and Buxton. They have the most upside, and potential trade value. This is an interesting concept. I like the head to head and roto scoring. I wish our league had a head to head element to it.

[Scott (Boston Padres)]

Thanks Chuck. Puig is a definite, already under contract. Bryant is also a definite since his keeper value is so good as I drafted him in final rounds last year. I just tonight started thinking of not keeping Buxton. Mid-round keeper and not even guaranteed to be in Majors this year. Now I'm leaning Posey and Desmond, each for one more year. So now my only real decision is Yasmany Tomas for 2 years as a 5th rounder (would slot down to 6th round if I keep Posey) or Danny Santana in the 15th round.

[Henry (Cleveland Nationals)]

Firstly, I'm not surprised you won your league last year- with these keeper options, what a team!!!

I gotta say I'm surprised Tomas in the 5th is even being considered. His Cuban stats show his plate discipline being a league below a lot of the other high profile defectors. Sure, there is power but he may not be able to tap into it properly if he is never pitched in the zone. His upside in my view is Mark Trumbo, and in the 5th (when he may also have a chunk of development time in the minors) is a lot to pay for that.

Having said that, I also see a bunch of regression in Santana, though I get SS is shallow. I agree with you completely on Posey and Desmond- definitely keep them!! There is an argument for Braun as I'm guessing with all those kept players the last pick in the first won't have the sorts of players you would usually see in the first. You're betting on an experimental surgery but the upside of even non-PED Braun is enormous. Or Duda in the 11th/12th? And of course Morneau in the 30th is bargainous. I'd be inclined to choose one of those 3...