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It's cheaper to influence a vendor the lower you level is. At lvl 1 you need 400g value to get to 100% approval at lvl 12 it's like 4500 or 5k.
So Dammon for instance it's much better to get max approval with him asap because he is also in act 2 and 3 (depending on how your story plays out).
I'm not sure if all of the Cha scores work toward discounts but I believe it will be based off the Skill (Deception, Intimidation, Performance, Persuasion) and not the Ability Score itself.
As far as using Enhance Ability for better prices, I don't think that it does. Enhance Ability only confers advantage on a roll using the ability chosen and does not add an actual score modifier.
If anything were going to work it would be Guidance as that adds to your scores but again it does so when a die is rolled and there isn't a roll when you enter the trade screen it just pulls the score off your character sheet. I think I tried it before and it didn't work.
Edit: There are times in the game where assisting a merchant leads to them offering a discount. Whether they actually provide a discount, and if so whether the discount is applied to the entire party or just the character that spoke with said merchant, I have no idea but it may be a mechanic.