My only concern is for the lack of size in CAT5 wiring. Also you only have 8 wires. He would need two use at least two fittings for each side. However, you are correct in your thoughts on the difficulty of connecting molex at times.
I've been using 28 gauge wire for ALL my control panels for years now, and never had a problem with it.
8 wires works great for modules.
A top-fire joystick, with TWO thumb buttons + ground, uses exactly 8 wires, and a 7-button layout uses a maximum of 8 if you don't wire a common connection for the 7th button.
I used 9-pin connectors on my swappable panels at first, and found they were a huge pain, for the reasons described above.
When I decided to go modular, I also swapped out to the RF-45 jacks.