1) Yes, you can use scaling in ESS and this can result in skew.
2) Over time as we have added features to PRO, we have provided the basic features in ESS. Eg, ESS used to not have auto key or ghosting, but now it does. Meshes (including FFD and weights) and IK are the primary reasons to use PRO. You can upgrade from ESS to PRO whenever you like. A lot can be done with ESS, eg check out Super Spineboy.
3) Yes, this is totally feasible. Eg, this video wasn't made with Spine, but it uses the technique:
https://dl.dropboxusercontent.com/u/18870395/flower.mp4
A potential downside is that the edges of your mesh can be jagged unless you can do some sort of antialiasing with your game toolkit.