Update 2/8/2015 - Unfornately, a few days after this post, Target changed their registers to not allow multiple loads in one swipe. See Frequent Miler and the comment left on the post for more information.
RedBird has become my favorite way to manufacture spend. You can spend up to $5,000 every month on any credit card at any Target register, including American Express gift cards, without any fees. The money then goes backs back into your checking account or is used to pay the credit card bill. You are left with just the points.
The only thing that's annoying is that there is a limit of $1,000 per transaction and $2,500 per day. That means that you have to load $1,000, then another 1k and then $500 to not violate the per transaction limit. This takes extra time and can lead to your credit card stopping the transaction due to possible fraud.
Yesterday, I went to Target and the gentlemen (big difference between a Target employee and Walmart employee) at the register asked me how much I want to load. I said $2,500, but $1,000 first and then $1,000 and then $500. He said, "You don't want to just do $2,500 at one time?" I asked him if he had done that before and he said yes so I said let's try it. I'm not sure exactly what he did, but he added a $1,000 purchase, $1,000 purchase and then another $500 purchase before I swiped anything. I swiped one time and it all loaded correctly.
I am sure not every employee will know how to do it, but it's worth a shot to ask.
I then checked Flyertalk and there is a report of this working as well.
So, that makes life a little easier.