I'll leave the flight analysis to someone else, but for credit cards, I would strongly consider the Starwood Amex (20k points would transfer to 25k AA miles, if you want, which would further transfer to 50k Hilton.) Many people think that SPG points are more valuable when used for their hotels, but they are very versatile nonetheless. You may also consider an AA credit card, for those places that don't take AmEx.

For hotels, I'd say Hilton is a good 1st choice program, as they have many brands and locations. I also use SPG and Marriott occasionally, depending on price, location and availability. Stick to earning hotel points, not miles for your stays - they add up quicker than you might think!