Here is the situation: I have many miles with many different airlines. I am planning two seperate trips I want to use my miles for, one June 9-17, 2007 to Grand Cayman, second one summer 2008 to Hawaii. There will be 4 of us and I would like us to fly together, if possible (2 kids and 2 adults). I know that I need to book my flight IND-GCM this Thursday night (right after midnight), but have never done it before and need help laying out the strategy.
1. I know that United is increasing points required in September or October, so would like to use these points first, but only have enough for 3 tickets. Should I buy miles for the forth one or try with Delta for the forth ticket?

2. How do I book return flight/when?

3. Should I just use Delta and use my United for Hawaii?

4. Could I combine my NWA account? Is it worth it?

5. Should I just let awardplanner handle the whole transaction for me? How much would this cost me?

Here is what I have today:

United Milage Plus:
Self: 123,148
DD: 500


DELTA
DH: 185,769
DD: 2,162

NWA World Perks
Self: 13,471
DH: 14,538
DD: 3,010
DS: 3,010


USAIRWAYS Divident Miles
Self: 14,320

Continental One Pass
DH: 1,267

Please help!!!!!!!!!!!!!!!!