The matching donor presumably wants the match to be used. So unless the match is often exhausted and I'd be displacing someone else's donation that would only be given if there were a match, it's in no one's interest (who supports the cause) to try to outsmart or prevent a virtuous cycle of donations. And there are generally just 2 states, a 1 for 1 match and a 0 for 1 match, so in the worst case, you can always save up your annual donations, and give them on December 31st if no match is forthcoming.

That said, if I weren't using credit to give, I'd use your system.

You can't time the market. The accepted strategy in a state of uncertainty is continuous, automatic investment. That's why I have a monthly donation set up, in addition to giving extra during matching periods.

You are referring to a general principle that has slightly negative relevance in this instance.