At the time of me obtaining this and writing this guide, I am very out of practice at chess. I've been playing Challenger and Amatuer games to (re-)learn strategy from the A.I. Eventually, I managed to beat the A.I., which has a much higher ELO rating than I do currently.
The lesson to be learned here is that you're better off playing against the A.I. that's outclassing you, as it'll be less hand-holdy than the easiest A.I. and when you finally manage to win, you'll get the various ELO rating achievements in the process.