Hi Sampson, I'm in the same boat as you. I'm looking at making a short film to test what I know too. I've found that the book 'Inspired 3D Short Film Production' by Jeremy Cantor and Pepe Valencia has answered a lot of my questions and problems that I've been pondering. It goes through all the steps involved in making a short chapter by chapter, and whilst it's not software specific, it really helped me to get an understanding of what putting together an entire short entails. I'd recommend that you get a copy (even just from a library or second hand book store as it is a little pricey {though I think it's worth its price three times over}) and check it out as it goes over a lot of your questions in depth.

Also I'd love to see you start a WIP here of this, I'd follow it with great interest. Would also help if you ran into problems and such. Good luck.