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I just read through all this and see three separate points be discussed:
 1. The unbounded caching behavior.
 2. A more compact representation for repeat counts.
 3. Correct __sizeof__ support for struct.
For issue (1) I think this is unfortunate, but I don't think any code changes are required because there is already a way to get the cached and uncached behavior by using the free function or a Struct object, respectively. I do think adjusting the documentation is appropriate.
As a side note, we do have a private function named 'struct._clearcache' that is used by the regression tests. If others really think the caching is a problem we could make that public.
Issues (2) and (3) are hijacking this issue IMO. However, since they are being discussed... I already implemented something like (2) when reworking the struct data structures for PEP 3118 in issue3132. Hopefully I will get the PEP 3118 patch pushed through one of these days.
I do think issue (3) should be fixed, but a separate issue should be opened for it. This issue should just address the caching behavior. Serhiy, if you open another issue for the __sizeof__ change, then I promise to review ASAP.