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@SSSasky
It's all really easy:
26" < 27.5" < (28" = 29") < 27"
Don't thank me. Thank the bike industry.
As far as the naming standards go, tires were often originally named for their outside diameter, regardless of rim size. That's why the name of the tire size often has little to no correlation to the bead diameter (the rim size).
Basically whoever made the first tire for a given rim named the tire size based on the outside dimensions, regardless of the fact that other tires that would share the same rim would not have the same outer diameter.