I'll try to address both your questions. I'm tired, so I might miss something...
1) Crankset. That's dependent on your legs and the terrain you ride in. My bike is 24-speed (8-spd cassette, triple crankset) and in theory it has climbing gears, but I suck at climbing!

There's a trend toward compact doubles for several reasons: 1)it's supposed to be easier to spin 2) you can accomplish the same spread of gears/gear ratios with less weight, and 3) shifting on a compact double is cleaner. And it's cheaper to manufacture and so the manufacturers have to pay less. Usually what they do is put some really huge cogs in the back so you get those climbing gears, and combined with a 10-speed cassette, they figure you're not going to lose much. They mostly sacrifice the high gears, but only a little. What can be a problem is that while there's a nice spread of gears, the jumps between gears are bigger. Your legs may not like that.
So no, triples on a road bike aren't a bad idea, but the industry--for whatever reason--is moving away from them.
2) Bikes, WSD.
All things being equal, if you can swing the extra $500, go for the Madone. Mmm, carbon.

Short legs, long torso
would generally mean that you can ride the unisex frame. Many shops steer women toward WSD bikes because that's what they're conditioned to do. 5'3" on a 50cm bike sounds a little big, perhaps, but I don't know your inseam. Your height might be a bit of a challenge when it comes to finding a unisex frame in the right size (48cm?). Go with what feels better. I'm the "ideal" candidate for WSD (long legs, short torso), but unisex aggressive frames with a 52-53cm top tube might be the best way for me to go because I have long arms. Ride everything, if you can. If there are reach issues with the brakes, it is possible to shim things.