What is the tongue weight on the rake in that picture? Can the Cub's drawbar carry that weight without bending and would it risk damage to the final drives? I noticed that Phil Lenke's rake has the extra wheels on the front to help bear the weight..
Eugene's answer pretty well covered what I would recommend. The newer rakes with the rear drive wheels are more gentle on the hay than the earlier ones with the front drive wheels. The front drive wheels are a carry over from horse-drawn days. The rear drive style would have needed a foretruck for horses. The tongue weight shouldn't be too much for a Cub.
As for tongue weight, most would not be a problem, but you should check it when you are looking at a prospective purchase. Most of our neighbors had New Holland rakes, that were no problem to pick up and hitch to the tractor. However, my dad bought a Massey Ferguson rake that had a tongue weight well over 100 pounds, took two people to lift it to hitch easily. One person could hitch it in a pinch, but it was an absolute bear.