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Group algebras are indeed twisted by 2-cocycles, but I believe this is a version of the group algebra that lives in C, so the associativity gets twisted by the associator.
Are we assuming X is chosen from the union of A_i with uniform probability? Even if so, we can only put bounds on the probability, since we don't seem to know the sizes of the intersections between the other sets.
Suspension shifts the dimension of singular chains up by one. One then runs into orientation considerations when gluing (as in Eric's question), and it changes their parity when looking at products.
I'm afraid cyclic groups are deceptively easy - one can find the Morita invariance classes with just a quadratic form calculation, with no visible topology. This also applies to a certain class of cocycles of abelian groups (Mason, Ng, math.QA/0002246). BG tends to get rather complicated at about the same level of complexity where these techniques fail.
I'm mostly looking for something that works. Since vector spaces don't detect extensions by BH, I guess it's categories or something with similar complexity.