TheMileageProfessor - Thanks for the useful info. That's good to know on the UA then US Airways awards booking.

How much do you generally spend when you go to the carribbean? What types of places do you stay at?

So I tried to put together an awards itenerary on UAL.com. I searched for all the individual city pairs first as one-way. I came up with this (just a possible itinerary, haven't decided on this yet):

DFW-HNL - 5/13/2013 -- 20,000 miles
UA5165 - DFW ->IAH 12:59pm
UA1646 - IAH -> LAX 5:00pm
UA1584 - LAX ->HNL 7:18pm


HNL-MFR 5/19/2013 -- 20,000 miles
UA72 - HNL-SFO 6:21am
UA6493 - SFO-MFR 9:15pm

MFR-DFW 5/22/2013 -- 12,500 miles
UA5643 - MFR-DEN 2:46pm
UA288 - DEN-DFW 7:48pm

When I tried to put it all into a multi-city, it didn't find a bunch of the options that I had just seen when I did one-ways. Shoudl I be searching 3 destinations (DFW->HNL, HNL->MFR, MFR->DFW) or each individual leg? I tried 3 and it didn't find an itinerary that fit. I tried to put in all the legs and it wouldn't give me enough spaces to add my last flight or two... Does this mean I would need to call to reserve?

wise2u - Thanks for the input. LOL, it's not granny, it's a bunch of friends who can't make it to the wedding so we may do a secondary reception there. Advice heard about not making it part of the itinerary. Will consider that for sure. I definitely will consider doing the Hawaii trip in the future after saving up more points. In your opinion, how many points (and what type) are needed to really do Hawaii right without breaking the bank?

Thanks!