[W. Deranged]

I think because of the most likely flow of the hand you have to lead out on the flop because you want to be the one putting in the third bet and facing a decision on the fourth rather than putting in the second and facing a decision on the third.

If you had led out, been raised, three-bet and then gotten four bet, a fold here is very straightforward. Because of the check-raise, you now put yourself in a position of having to make a decision for a very large amount (not just the $550 but more because you may decide to four bet the flop and/or put more money in on later streets) without sufficient information. By leading and the reraising, you put in more money but get much more information out of it, and I think the value of being able to save yourself because villain puts in a third raise far outweighs the extra cost.