Yes and no.
Once you get an SE/30, you'll definitely want Mode32. However, a Classic II only supports 10MB of physical memory (the 2MB on the board + 2 4MB SIMMs) so Mode32 is superfluous for that machine.
If you go the Classic II route, I don't advise trying your luck with System 7.5 - use 7.1 or 6.0.8L or you'll just be torturing yourself.