Talk about money hungry -- and stupid! IMO, all of the people who really know anything about hacking areright now. If Jon could hack into a bank's database, he wouldn't be doing Vegas for $15,000 for a weekend's work.
The email one -- I think that's doable.
On Nancy Grace a few days ago, she asked one of her experts about whether Jon could do this. They said that based on Jon's IT background, it would be easy for him to look up what Kate did on the household computer, extract deleted stuff, etc. All he needed was to find login information, not hack through a bank's security system. However, I don't know if its true since Kate might have her own computer or laptop that she locks up or travels with.