Originally Posted by
regoarrarr
(EDIT I know this is long: tl;dr
I live in northern Cincinnati, so about equidistant between CVG and DAY. I came up with the following
JFK-MAD-MXP-LHR-ORD-LAX-SYD-DFW-DAY-DFW-HNL-ORD-CVG-MIA-CUN-ORD 39336 miles - any issues with that?)
You could do all this and not have to do the positioning flights for at the most 195k AA. If you are good with the stopover rules, you could get the outbound for your Hawaii trip for free, bringing it down to 172.5k miles needed plus positioning flights.
And you couldn't book ANYTHING until 365 days before the last flight. Even then, you'd have to book a bunch of dummy flights at no more than 330 days out for the Cancun trip then move them once the flights open up.
Explorer awards are generally good for one main thing - stopovers at every destination. If you are hopping around Europe or Asia and staying for 2-3 days at each place, it's awesome.
There are a few rare cases where you are better off using an Explorer award for single destination travel but this doesn't appear to be one of them.