Accept challenge. Price out what it would cost to get a therapist or a sorcerer or something to give Leon a positive trait or two.
After asking around for quite some time you are somewhat surprised to find that there IS a man who is willing to do the 'operation' as he puts it. The only issue is that it'll cost you a hefty price of 40 gold pieces. Even it'll change both of Leon's personality traits. The man states he might be persuaded to only affect one at the cost of 60 gold pieces.
Accept. Train Bucky for further girth!
You head out to buy Bucky as much food as possible but you're not entirely sure how much money you're wanting to spend on this...
look for an animal training school to fight, preferably average-hard in strength range.
The Green Artisans have a Wolf that they have been wanting to test out. Unfortunately it would likely destroy your entire roster in a few moments. The wolves of Centria are well known for their deadly abilities... Still... That's the weakest animal you could find. Unless you count goblins, which some do.
Visit the tenderfoot and peruse potions.
"So... I guess I got turned down?"
"Well... You've seen my team right?"
"Yeah, a bunch of weak peasants and, from what I've heard, a squire in training. Not even a fully fledged squire."
"Exactly. Do you want those only one of them protecting you from a Hill Giant? My facilities aren't large enough to handle three gladiators."
"Hm... You make a good point. So I suppose you're here for some potions?"
"Yes, my good tenderfoot, I'm looking for your most powerful potions."
"Then look elsewhere. We've had this discussion before, I'll sell you what's legal to sell you and nothing more."
"What?"
"You think they let anyone buy anything? No, it's a long list of tiers and a bunch of things that aren't really worth explaining. Here..." The Tenderfoot spends several moments writing something down before handing it to you "This is what you can buy from me for now. I don't actually sell the last two items on the list. But if you happened to leave some money on the counter well... Who knows what might happen?"
Treebark Potion - 200gp
[abbr]Adds 15% accuracy for one battle to one gladiator. Consumable.]Striking Potion - 200[/abbr]
Weakness Poison - 200gp
Darkberry Poison - 150gp
"This is... pretty expensive..." is all you can say to the small list.
"They are... They're expensive to make because of the damned Alchemists guild. But some schools buy them by the literal boat-full so maybe the price becomes easier to deal with over time? I don't know. I'm just a tenderfoot."
"Well... I'll take this with me and consider it."
If there is time for training, spend enough to boost Ugly to the next level (3xp shouldn't be hard to come by).
You spend 2 gold training Ugly Jerry but no matter what he doesn't seem to get any better after that... Which is odd... It doesn't make logical sense but... You figure he just needs to take part in a battle to unlock his inner potential... Maybe?
(what are the levels of difficulty? have you a roster of low level schools with 2-3 gladiators, besides the player schools?) If there is time for training, spend enough to boost Ugly to the next level (3xp shouldn't be hard to come by).
I do not, currently, have a roster of low level schools but I do have all the gladiator types sorted by fame-level as well as by health, damage, and armor. So I just select them randomly, adjust the challenge accordingly, randomly generate a name and off you go. You can pick Very Easy, Easy, Moderate, Difficult, Very Difficult, and Impossible. Only Impossible should require explanation. You CAN win an impossible fight, but you're gonna have a tough time and likely lose.