Maybe a dumb question but if I am understand this correctly you 301 redirect to your money site and watch it rank, when it inevitably passes on a penalty you then take the site you had just ranked and redirect it too, correct?
If this is true, why do you bother? Your initial redirects already have proven to rank you for you keywords. Do you see even BETTER rankings after redirecting the newly penalized site too? You are not concerned that the additional redirect(s) will pass a penalty sooner? (3, 4, 5 or more penalized domains passing juice instead of just the initial 2)
Thanks for the great thread!