The trouble with having the IM search for an English-speaking program is that the search basically has to be done by iterating over all programs and running some acceptance criterion over each of them. So if you wanted it to find an English-speaking program, you'd have to have already written an acceptance tester capable of recognising a genuinely English-speaking program, as opposed to one which was merely cheating in some way. In particular, you couldn't define an English-speaking program as one which would give specific answers to some finite set of test questions, because almost certainly the shortest program capable of giving those answers to those questions would be one that simply had them hardwired in in some fashion. So I fear that one might be infeasible.

Chess shouldn't be a problem, though. You could certainly find out which player won in perfectly played chess, and you might also try searching for the shortest program capable of producing perfect play within reasonable execution time, to see if it turned out that there was a relatively simple way to make the optimal strategy practically implementable. (As there is in nim, for instance. Presumably for chess it would be far more complex than that, but it might still turn out to be tractable by a finite computer.)

I think I'd be more interested in asking about go than chess, but that's just me.