Yes they will (most of times). One thing to remember: Taobao is entirely third party sellers. Nothing you buy come from Taobao itself. So from item to item, the terms vary quite a bit.

mostly, but I don't think all?? The TMall section is large retail stores - it's the equivalent of buying from a large high-street retailer. Some of them are shipping thousands of packages a day, so you can place some faith in them (ie. at least 110+ stores made more than 10million RMB in a day, so it's not like buying from a street market trader.)

There are companies setup that will buy things for you on taobao and ship them to you overseas. They help with customs etc and have sites in English. Google 'taobao english' and/or 'taobao agent'