2 Cents
I did my PPL in the H300 and then did IR/CPL in the 22 and 44. Here are my thoughts on the two.
H300 -
The good - Very stable. Very forgiving. Easy energy management in the rotors during auto rotation. Handles high (20-30kt) winds well.
The bad - Long start up and shut down. No governor. Seats are more upright which is uncomfortable after a long flight.
R22/44 -
The good - Has a governor. Fast top speed. Quick start up and shut down. Comfortable seat position. Can store things under the seat. Very effective tail rotor.
The bad - Very sensitive controls (requires finesse). Energy management more difficult (rotor speed increases/decreases rapidly in autorotation). Harder to handle in higher winds.
From my experience, the H300 is much easier to learn on. During my transition to the 22/44 after getting my PPL, I felt like a brand new student again. It was rather difficult to learn to hover and become comfortable with it. However, once I became comfortable with the robbie, I found I really enjoy it. It is great helicopter. Both helis have the ups and downs.
In short, the 300 is easier to handle while being forgiving, and the 22/44 is fast and comfortable but requires more skill from the pilot.
-cheers
---sidenote, the 44 is easier to manage rotor rpm than the 22---