Originally Posted by Stubtify

My estimate based on your credit score is that you may only get to apply for 2 credit cards here. Make them count.

I would put more focus on where you want to stay, and what hotels and hotel points/$$$ you will need to spend to do so. Put together a budget, with each item 2 different ways:

Flights: If you spend $$$ // If you spend Points

Hotels: If you Spend $$$ // If you spend points

You already have enough miles for one flight, so maybe buy the other flight with cash and focus on Hotel points? See which way ends up with you spending the least out of pocket, assuming you can only get 2 credit cards. Then try for cards 3&4 and if those come through, great. If not at least you've reduced your OOP expense the most you possibly could.

If you're doing 8 nights @$150 a night you'd be better off to just buy a flight, even if it costs you $800 as long as you can swing all those nights for free. Try to rethink the overall expenses and keep your costs as low as possible.

An Example:

Buy one ticket, redeem your current miles for another. This costs you $800 for the flight

Fly open Jaw, into HNL, then redeem 5k/7.5k delta miles for a flight to Maui, and fly home from there? Buying one flight gives you miles for these intra-island flights with what you already have in your delta account.

Apply for SPG Amex card, and Hyatt card and focus your spending for the next months there. Look for SPG C&P rates or 5 for 4 rates if you can get up to the needed point level.

It is really risky to do any of this without the miles already in your accounts, because you're "guessing" at what availability will be there when you actually go to book. If availability changes after you get your points a backup plan would be to surprise your wife with the details of the trip on your anniversary, and plan it to be at a date a few months in the future. Your wife gets to be excited for her trip for a few months and you can make sure you get to book C&P rates, and lowest award redemption levels. Trying to fit a trip into specific dates is hard enough when you already have the points, to do it like this might be setting yourself up for disappointment.