M, Q, D

[PantsOnFire]

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What I'm concerned with in a tourney, when it comes to an all-in decision that will potentially send me to the rail, is this: is it worth taking a 60% the best of it here for my whole stack? If I go all-in as a 60-40 favorite four times, and someone has me covered each time, my chances of going to the rail are a whopping 87%.

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Your question has many facets, but I'll address the above. You didn't take this analysis far enough. You need to look at what your results are in the 13% of the time you survive. Winning four consecutive all-ins when covered results in a stack that is 16 times larger than when you started. So you now need to figure out how often and how much that converts to payouts.

A sixteen-fold bigger stack than starting stack represents an average stack when the field has been cut in half four times. This would mean you are averaging a Q of 1 well into the money. That actually sounds pretty good to me.