Yes I agree. Definately get a flat bed scanner if you don't already have one. Your art doesn't look like it's photographed though so you probably already have a good scanner.

As for software, I suggest getting something free like Open Canvas as D suggested to see if you really like doing digital work before you invest a lot of money.

Don't expect the computer to do the work for you though. Just because you are doing art on the computer, doesn't mean it takes any less skill than doing it by hand. Even though the computer offers some nice convenient controls that speed up the process when compared to doing things traditionally, you still have to use the same hand to make the art and have the same eye for design/color/porportion/etc.

BTW, does the programs out there, also apply the shadows n' stuff where needed, like I see on most pictures, or do you do that by hand?

As far as I know, the software won't add shadows for you, unless you are refering to a simple drop shadow or if you are working with 3D software which is an entirely different thing.