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Good question. The timeline for clients is less critical, as long as a majority of hashing power will properly interpret OP_EVAL clients that relay/generate those transactions can be rolled out anytime after Feb 1.
So I'd suggest releasing a 0.5.something or 0.6 after the Jan 15 "are the big miners on board" evaluation that turns on OP_EVAL support Feb 1.
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Same time.
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Another very good question. The timestamp in the block will be used to determine whether OP_NOP1s in the block are interpreted as no-ops or OP_EVAL when checking block validitity (wall-clock GMT time will be used to figure out if the node should relay/mine OP_EVAL transactions). I'll double-check my code, I think I did NOT code it that way.
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That seems exceedingly unlikely; once the big mining pools switch, there is a very strong incentive for the smaller pools to switch, too.