1. I initially didn't change the stem, but later I flipped it so that the stem was more level with the ground. At its stock position it was very comfortable, but now it rides more aggressive and looks better. I now have a Ritchey stem, but it's the exact same size and everything (just flashier).
2. I would say it is about the same, but with a bit more sportiness to it. I think it is a good progression from the casual neighborhood rider to something a bit more aggressive.
3. It is a bit tricky at first to move your hand down to shift, but you get used to it pretty quickly. Brifters are ideal (brakes and shifters in one unit, like a road bike), but they're CRAZY expensive, hence why I chose the barcon shifters.
I think you'll like a drop bar conversion. I do miss having flat bars and the simplicity of just riding casually, but I also love being able to get out there and hit the pavement going strong.