I would really like to believe that Ging just on the spot decided to set himself in the worst light possible, and this way provoke Leorio to act and by doing so focus some support from the community on him. As long as it's opposing Pariston's goals, it works. And nothing to do with bad parenting, guilt trips and deserved punishment. At least, not directly.
I'd bet on it. He apparently has some ability at foresight; perhaps it's his Nen ability. Think about it. He predicted exactly how Pariston and the other Zodiac would react during their discussion on electing a new chairman, and he was very adamant to Pariston that Gon would live. My guess is that he has something similar to Neon's Nen ability, without the need to write down his predictions. Perhaps he knew that Leorio (or any of Gon's friends, really) would come to see the election debates and directly confront him, and he openly provoked that to increase voter turnout and get votes away from Pariston.
Personally, I'd rather see Cheadle win the election than Leorio. Leorio winning means he's stuck at a desk, can't become a doctor, and also can't be part of the main cast again. Despite being a new character, Cheadle is likeable enough to be the new Chairman, and would get things done a lot better than Leorio could, and would definitely be better than that slimeball Pariston.