#1
ok, so I own a fender MIM standard strat and usually use d'addario lights on it. One problem i have encountered lately is that i break the 1st-3rd strings (the bottom ones). I seem to bend them to far and they snap. so my question - is there something wrong with my bridge setup or something, or do i need a higher gauge set of strings (if so, suggestions are extremely helpful)

and i don't plan on stopping my bending.
#2
the daddario's are your problem; brittle, expensive, and week toned imo and they dont keep there so called tone for very long either. you might also, like you said go with a thicker gage, but since its a floating trem that may cause you more trouble than its worth. i know a lot would disagree with this opinion but i highly suggest a change in string brands, ive had nothing but duds come out of those overpriced daddario bags
#4
these http://www.curtmangan.com/products.php are the best, cheapest strings ive ever come across. Ive actually met curt, hes an awesome guy, and his strings are durable as hell and have a great tone. unfortunately since ive moved to nevada i havent been able to get ahold of them, i think they have a retail locater thing on the site so you can try your luck.