I am all in favor of doing what is reasonable to maximize the mileage/points game, but visiting a Simon Mall, going to a CVS, and then heading to a store to cash out the Vanilla's is not worth my time. This is far too much work for a $25 gain. Even if you can scale up the process, what is being described would consume more than an hour based on my locations.
I suppose based on your proximity to Simon, CVS, and your money order vendor, it may be worth it.