Ok, as far as crush, it looked pretty good to me... not that I have much experience with it, but it seemed to be cracked open well (say a little smaller than steel cut oats, if that helps).
I did pre-heat the MLT; I heated my strike water to about 10 deg. above the strike temp Beersmith gave me and waited until it came down to strike temp inside the MLT. After I added the grain and stirred everything up I measured the temp and it was right on.
The only issue I see with this cooler is that the lid has no insulation, it's just a single layer of plastic that screws on... that may be where all my heat went. Unfortunately with the 2 gallon cooler I filled it just about to the top with 5 lbs of grain plus water, so there's no room to throw some insulation on top. Could I use a 5 gallon igloo cooler for 2.5 gallon batches? Would that give me enough grain bed?
I mashed for an hour and batch sparged at 168 deg.
I did adjust my hydrometer readings, and after adjusting with DME my OG was right where I wanted it. (at least I have math skills if not brewing skills yet)
Thanks for all the replies.