Will saw in Ben Quick a younger version of himself. Yes, he would much preferred someone as ruthless as he was as the next generation. Jody just doesn't have that killer instinct in him, or until he tried to kill Will which demonstrate his drive.

I don't think he was truly stupid. Not a brain trust, either, but he probably would have been much more functional and a higher achiever with a different kind of dad.
Timid, insecure kid raised up and ground down by a boisterous, hot-tempered brutish blowhard. Same kid would've turned out completely differently if he'd been born to a couple of soft-spoken intellectuals.

I think he was intelligent but was so nervous about filling his father's shoes, he didn't use better judgement and he was insanely jealous of Ben Quick which further clouded his judgement.

I think he was more needy than stupid. When the father was in the hospital for those few months,the son looked after all the businesses,and things were great.