I try to evenly weigh the destination, the airlines/aircraft, and the hotels.
That's a good point, too.
I'm not about to drop $500/night at a hotel in places where there are no points-hotels.
So I guess, for me, it's a combination of picking the farthest destinations (most bang for buck), with the best points hotels (don't wanna drop $3-4k for a week's stay), and then picking the most attractive destination from what's left.
When I'm finished with that, I can hit up AA's new A319 in F to LAX