Ithink this is a good candidate for either the Starwood Amex(plat.if you can swing it,the Aeroplan Amex(since you could book *alience partners). the Capitol one Platinum no hassles milage card.or a Diners Club card.Since you have five different airports,none of which are a hub,and so you are going to need a lot of flexibility/availibility.And all of the above will let you have additional cards for family members.
I am going on the assumption that AC is still a partner with Amex platinum and Diners Club.