Good points, plaw and yes, my hypothetical question is not really hypothetical and money is involved!
I know, rationally, you are correct - you and I being like-minded in terms of numbers, expected value and such. My gut says though, that it's sort of pansy to turn in different brackets in different pools. I don't know if it's my conscience or whatnot, but for some reason, I feel uneasy about turning in a bracket that I don't feel is my best pick set. That's just something I have to get over. In the end, it's all about strategy. Just like in fantasy baseball or basketball, I might pick a team towards the end that might not be the best team possible but makes sense in a tight race (just like the end of the first half of basketball). Choosing different brackets is just another strategy. It's just like in investing - you have to diversify to hedge your risks.
Any other opinions? I'm sure some of you are running into the same situation. You may not analyze it as much as plaw and me (who over-analyze everything ), but let me know what you think.