A huge obstacle that we face is his motivation. It is easier to fail than to try. And my son is very good at finding reasons to fail.
And today was an example. Leaving school he and I were catching Pokémon and I caught a shiny Evee. When in Madeira we had caught quite a few, well, he did. I did not, but despite that he wants mine as it will complete his collection. Needless to say, I want it, but it is a game and he is my son. When he said that he would do anything I wanted, I gave him a task, to pass the questions we give him, scoring 100% every day for a week. Needless to say, he felt it was too strict and since being at home with my wife, we have settled on him getting 85% for 14 consecutive days. And I do think that he can do it.