When I first started I had a Wacom Bamboo Fun which I absolutely loved. It was somewhere around a hundred dollars but it could be cheaper now. I also had an Intuos small which was also very good and should run cheaper now. Anything by wacom should do you good, and they're pen tablets aren't as expensive as their on screen tablets. Some companies don't update their drivers enough and/or don't support certain programs is what I've seen happen to people. I've heard the Bosto kingtee company has that problem////
Any program would be fine. I've used Paint Tool Sai, FireAlpaca, Manga Studio EX 4/5, Clip Studio Paint EX and they're all really good programs. Photoshop I mostly use for final effects on drawings, I sometimes use it for background making. It's just all about your preference though. Try out some of the programs trials and see which one your comfortable with.~