My husband and I would like to celebrate our 20th anniversary next August in Hawaii (specific island tbd). We'll consider going in September for off peak advantages. I'm needing help strategizing my next round of cc apps to collect miles/points for free flights and hotels. Current Cards and Programs : 1) BA Avios~127K (don't want to use these for this trip b/c I no longer have means to collect avios; wanna use these for family vacay) 2) CSP~8K (recently used 83K for cruise flight to SJU) 3) Citi Hilton Visa~89K First to consider: flights. 70,000 AA miles or 80,000 +$20 UA miles to get us there. The Citi AA cards or Chase United don't seem to have stellar sign up bonuses right now (wasn't in this game when the 50K AA was available). Should I wait for a better offer to come along? OR Southwest is another airline nearby. I've read of one strategy of applying for that card (would wait til first of yr), and also apply for Hawaiian Airlines card. Take SW flight to West coast, the HA to HI. I haven't run the number of miles this would require. Second: hotels. Definitely applying for Starwood card, either for hotel or transfer to AA. But, since we have so many Hhonors points, should i try and stock up on these points with another Hilton card (Reserve for 2 free wknd nights)? Or should I consider Hyatt? I am leaning toward the Big Island, but not impressed with the Hilton options there. I would love to replenish my UR account so I could transfer to UA or Hyatt. I would love to apply for the Ink Bold or Plus, but I feel I would be stretching the truth to apply as a business (I would NEVER lie on an app), since the only thing I do is sell on eBay occasionally. Just doesn't seem legitimate. Other Chase options? I tried applying for my own CSP using my individual income back in March and was denied. Could I try again using our household income for better success? So many options, so many decisions.....it's driving me crazy! Any suggestions would be greatly appreciated!