This brings to light a nomenclature absurity. if you have "Squirrel" and "Squirrel HM" you'd expect no matter what your Equipment level "Squirrel HM" to be difficult. It isn't.

SE should probably get around to renaming Hard and Extreme Mode content to something more appropriate:
"Squirrel - Advanced/Epic"
"Squirrel - 55/90"

These surely imply more difficulty, without being dishonest.