Hello. Yes, this is possible, but you can only transmit MIDI from the H90’s DIN output, not USB.

Your settings look correct. If you have an expression pedal connected to the H90’s exp input 1, when you adjust the expression pedal, that should be outputting MIDI CC 1.

Can you try using a MIDI monitoring app and seeing if the MIDI CC information shows up there? Something like this should work fine: https://www.snoize.com/MIDIMonitor/