Originally Posted by smedleyb

I say start with the free cards (AMEX Hilton, CITI Honors Hilton, roughly 100-115K when taken together), then work up to the Citi Reserve Card, the 2X35K Hawaiian Air cards (BOA, and BOH), all of which have fees (but which give you two Hilton points for each HA point transferred).

Stage two, bump up the AMEX to the surpass (and get the second bonus of 60K), keep an eye out for the 65K Virgin Atlantic card from BOA (which also is a good (2X) transfer partner with Hilton), and if spend in not a problem, go for Diamond via the Reserve card (spend 40K in a year) to achieve real status and upgrades (not impressed with my Hilton gold status. All it seems to get me is free water).

Good luck.