Assuming no legitimate ways exist, what are "gray area" ways of doing this?

To clarify, I would like to generate spend on a credit card and am perfectly happy having to pay 2.5-4% of the amount I am spending as long as it does not cause a Financial Review flag or any other kind of suspicion from the issuer.

I understand that I can pay mortgage/rent/etc. via WilliamPaid/ChargeSmart, but I am looking for ways to move more than a thousand dollars a month.

Thanks!