Wife an I are 5 day reserved DFW/HNL in first milesaver on 8/4/15 due to 2 being available. Only 1 is available on 8/5 which is the date I would prefer.

Opinions as to wether it would be better to book the 8/4 flights and wait to see if a second opens up on 8/5 or should I grab the 1 on 8/5 and book the second as anytime and wait to see if a second milesaver opens on 8/5 and rebook on the anytime to milesaver?

Second option.

Cancel the 2 milesaver first on 8/5 and hope that they are returned to inventory and retold for another 5 days? Would I have any better luck calling AA EXP line and asking for them to retold for another 5 days?

Anyone have any guess as to what the time frame for opening a second milesaver might be?

It is interesting to me that all of the flights have 1 milesaver when the Tuesday flight had 2. Seat management I am sure.

Didn't have this problem 2 years ago when we booked. 2 always seemed to be the minimum available at start.

Based on some things that seemed to work for me this summer,

Try making mileage saver reservations as one-way travel. Get the two secured one way trips reserved that you know you want.

Then, if the preferred date is really preferred, get that one-way award and just plan on buying the lone single one-way ticket if the other award doesn't open up.

You might also decide to check if business class mileage saver awards are available on your preferred day. They'll cost more miles, but you might enjoy that experience and then you'll know you have all your tickets for next Aug.

It depends what you mean by "prefer". If you're EXP and have lots of miles, then ticket all three seats (2x4th, 1x5th); if another on the 5th comes up, then ticket it and cancel the 2x4th; if not then cancel the single on 5th.

If "prefer" means you're really going to fly on the 5th, even if one is milesaaver and one is aanytime, then forget about the 4th.

Jridge. Interesting thought. That is a cool strategy if it will work.

Will the system allow me to have 2 booked tickets on virtually the same itinerary at the same time? Previously I have had a reservation like this. Wanted to get the second reservation before canceling the first and before I could cancel the first the system auto cancelled the second as a conflict. And when I say auto cancelled I mean within the time it took me to change screens and hit the cancel button.

And yes. I will fly the 4th. I refuse to pay 90k for a ticket worth 37.5k if I don't have to. Another day in Hawaii. Oh pity me. LOL!

And just for kicks. I am trying to figure out how to delay booking for a couple of weeks to get enough miles just to see 1,000,000 miles in my account. Oh everyone should feel so sorry for me I know. ROFLMBFAO!

If the flights overlap then it is a speculative booking and it is not allowed.

But if you're doing one on the 4th and another on the 5th, they wouldn't be "at the same time", right? In theory, you could still even fly back to DFW on the 4th and take the flight on the 5th.