I went straight for a dual action. I think its a Paasche VL. I didnt find it difficult to figure it out, just paint some pieces of cardboard and play with the air pressure knob on the compressor until it sprays what you want (all paint brands are a bit different). All the way down and all the way back and it's the same thing as a single action. But if you want to do weathering and what not, then you start fiddling with the paint mix in the air stream. Its not difficult to learn, and I agree with the comments above to just buy a decent one from the get go. A good tool is cheaper (and less frustrating) than blobbing a paint job on something and having to fix it.
As far as the booth, i got one off Mr. Bezos' website that you can vent out the window. Check the dimensions of them. Some of them are too small to genuinely use with O scale trains. The one I have is marginally sized for O scale stuff (its like 21x12), you can get huge ones but they cost big bucks. Even with the booth, get yourself a respirator to paint with.
Paint is personal preference. I've sprayed a lot of trucolor and a lot of scalecoat. I prefer the paint job you get from scalecoat, but the thinner is pretty nasty stuff (its xylene based) and it takes forever to dry. Trucolor dries really fast, the paint job is decent and the thinner is a much more tolerable acetone based formulation. There are many acrylics out there now as well that you can paint with that probably clean up with some very nice thinners (i've heard some can be cut with stuff like windex). I've not tried them.