I pretty much exclusively draw on paper and I want an easy gateway into drawing digital. Should I stop being cheap and buy a tablet or is there a better way of doing it? Also is there a good program for it because the one I downloaded only gives you 3 fucking layers.
If you're at all serious about digital, a tablet is a necessity...but you don't need an expensive one. As long as it has pressure sensitivity, its good to go.
SAI Paint Tool is a popular one but doesn't seem to work with a lot of tablets, especially cheap ones. Do your research.
Manga Studio/Clip Studio Paint is a really great alternative, but my personal preference is Photoshop. Both are insanely expensive though, so either search for free alternatives or hop into the wondrous world of pirating.