From a womans perspective - here is my take on sandals.
I have Chacos with the toe loop - HATE that thing, maybe I would like the one without but spent so much on them I haven't gotten around to getting another pair.
Teva - not as much sole support as the Keens. I wore Teva's for years as a professional gardener, have worn them hiking with no problems, but they aren't so great on concrete. My feet really ache after a day at Disney in Tevas.
Keens - just bought my first pair. Not sure yet. Pricey, but they offer great support, comfortable straps, and expecially the H2's should dry super fast.
Birkenstock. Ok, if he won't wear Crocs, maybe he won't wear Birks. But for support, Birks are great! They don't dry as fast as other sandals, but I've done WDW in birks and left with happy feet.
Overall, my latest strategy is to take as many pairs of shoes as possible. Switching off is the key for me. So tennis shoes are great for a non water ride day, sandals another day, etc.
Happy shoe shopping everyone!