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There was a replicated experiment done here not too long ago on stropping. The results seem to indicate that 60 passes on the strop is about the optimum to keep the razor sharp the longest time.
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In short:
1) yes (but you'll likely be bitten by one or more acquisition bugs anyway)
2) before each shave (some strop between passes during a shave as well, others strop after too--I do neither)....