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It seems to me you're an aspiring Visual Novel developer. If you're having trouble drawing characters for your games, you can always just commision someone like me to do this work for you. If you want to do it yourself, I'd suggest you first get a good grasp of drawing people, or anime characters specifically. It's going to take a lot of work. Search youtube for beginner tutorials on drawing characters, and most importantly copy a lot of screenshots from your favourite anime / the anime which artstyle you see most fitting for your projects. Copying will help you understand how to draw - don't use these copied practice drawings in your projects tho :D 

When it comes to drawing digitally, any software which can save pngs with a transparent background will do - Photoshop, SAI, etc. Even newer Paint versions can do that I believe.

Good luck