Kenny Rogers: political philsopher

My turn to join in the ever-expanding chorus of folks offering President-elect Obama advice.
My advice isn't related to policy, but to process.

Kenny Rogers had some good advice:

You got to know when to hold em, know when to fold em,
Know when to walk away and know when to run.
[Kenny Rogers, The Gambler]

I've in mind a few specific situations requiring this counsel:

foreign policy

Iraq
Afghanistan

Bailout

AIG
General Motors

Focusing on the economic/bailout cases: what informs the decision? (Hold 'em, fold 'em, walk away, run?)

I'd really like to see a serious cost/benefit analysis from someone - GAO, CBO? (Independent analysis preferred!)
We're already seeing that the original bailout of AIG has failed - even tho' it was deemed more than sufficient at the time.
How much more is likely to be needed to keep AIG afloat?
Will any amount be sufficient?
What would be the effect of AIG failure? (I note that we have a smaller case-study available: Lehman. The world did not come to an end; the market really did quickly manage to value Lehman's assets.)

Same analysis for GM: What's the likely total cost to "rescue" GM?
Can GM honestly be rescued?
What is the cost of GM failure?

One component of "cost of rescue" is opportunity loss: What else could be done with the $$$?
Would the proposed $$$ be better spent mitigating the effects of failure?

If I start quoting Hank Williams, it's probably time to stop reading AQA.