I think Holliday/Lester for Miggy/Danks is fine deal value-wise, however, I'd be a bit concerned about what it does to your roster flexibility. It would leave you with Berkman at 1B (I'm assuming he qualifies there in your league), and FIVE players who are strictly OFs. Berkman is obviously a big injury risk, and losing him could be a big blow to your team.
I really like the 2nd deal for you. I see it as something like this:
Holliday < Miggy
Lester >>> Ogando
Ellsbury >> Jones (Adam Jones, right?)
Posey >> Buck
Kimbrel >> Roberts
Four significant upgrades, and the price you pay for that is just to replace Miggy with Holliday.
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