Basically, what my question boils down to is:
Which is likely to provide better "cushioning" on a given run?
a) A shoe designed to give lots of "cushioning", but that's already got lots of mileage on it (let's say 300-400 miles)
or
b) A shoe that's not really designed to "cushion" much, but is fairly new (let's say 30-40 miles)
I suppose it might vary depending on the exact models of shoes we're talking about, the person's weight, and stuff like that... but I'm trying to get a general understanding of how this works, so any input would be helpful.