WOW.  I am so impressed.  that's genius about the office supply store and gift cards.  And thank you for mentioning the Chase quadfecta.. this makes sense to me now!  Ok, so now I know what I am shooting for but the question is the order in which I proceed...
I agree.. nothing like a good pro/con list!! 

  I would love your opinion.. let me give you some more info!  So I do plan to spend the $5K rather quickly as my ex is taking all the bedroom furniture and the kitchen set.  So as soon as I get my card, I'm buying.   Likewise I want to secure my DVC rental ASAP so as soon as I get a card, I am ready to book that as well.  These two things will come out of my savings, so I have that cash on hand, but really should not spend more than that at this time.  So that leaves my normal "everyday" spending that I would put on a credit card and that's about $1500 a month. 
So in 90 days the max I could do is about 10000?  I need to be smart and conservative so I agree, I don't know that I can just jump in and over-extend myself.  What do you recommend in this situation to start with?