Remember that, officially, reservations made on Marriott's cheaper "Advanced Purchase Rates (APR)" cannot be paid by gift cards.
Please check out
Mooper's thread and my post in there (
#66) referencing this.
Your logic of leveraging Chase Ink Bold's category bonus:
Originally Posted by
BoilerHack
...purchasing $1000 of Marriott gift cards from Staples.com and getting the 5x Ink Bold bonus and 4x Staples.com bonus.
... is novel, but I'm not sure if Chase is going to allow the category and shopping bonus to stack.