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My head hurts just thinking about this one!
How about taking the infractions in the order they happened...
Enforce the illegal pitch first. The offensive coach gets the option of the result of the play or the illegal pitch penalty.
If he chooses the IP penalty, the result of the play (catcher's obstruction) is moot. You can't enforce the CO penalty. End result is runner on third, a ball added to the batter's count. (If it's ball four, the batter gets first base, too).
If he chooses the result of the play, then you enforce the CO. The IP is ignored. End result is B/R placed on first, other runner stays on second base.
Now that I think about this some more...wouldn't the end result be the same if you enforced the CO first? You can't enforce both the CO and the IP, since in either case the other one would be "the result of the play". After it all shakes out, the coach gets to pick one or the other and can pick the one that he feels gives his team the best advantage.
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