Having skill depend on money is a bit of a dodgy idea, because Swimmers have a very low amount of money because of their lack of pockets, Burglars have lots of money because they stole it, and Ladies just have huge wads - none of these facts should imply their relative strengths at being trainers. At the moment skill/money levels don't affect too much, but may do in future, so this may become important.
Bear in mind that wild Pokémon don't do any AI calculations. Each of their moves has an equal change of being used.
AI isn't mentioned anywhere in any great details because it's one of those fiddly things that people aren't expected to touch (although admittedly it's simpler than it could be). I believe you expressed interest in developing the AI in the past, and I'd be perfectly willing to help you with that. I don't have any experience with balancing, which is really what this is, so I'd need others to say what is acceptable behaviour for different tiers of AI (and indeed to invent those tiers). It's a topic for another thread, though.