Me to.. But i have a hard time working with vectors. Heard that Illustrator was the way to go, but i only have knowledge of Photoshop. So your iconset with the birds are all photoshop? Vectors? Do enlighten me.
imho, Photoshop is easier for vectors than illustrator for me. Even when i design logos or vector illustrations, i use photoshop, and then export all shapes to illustrator. it's a bit weird, but that's how i'm used to do.
Birdies are all vectors, on 1024x1024px canvas, but all done as layers with shape masks in photoshop. I only have 2-3 raster layers, for some blurs and details.
Illustrator is great for vectors, but i prefer Photshop because it's vector capabilities are pretty basic, therefore they are easier to master. Plus, you can never get blending effects in illustrator as you can in photoshop..
I hate pen tool as well, but here's what i do: i don't draw anything with pen, i usually take shape that is similar to the shape i need, and then i add or remove anchors with pen tool, and get what i want in the end As for Illustrator and transparency - well, you can always make template with gray and white squares, to use as transparency layer I'm self taught as well, i know how it is. If you need any help, feel free to ask