I begun with Leo at the same time I begun with Python, and also found Leo a bit overwhelming to use in the beginning, but Edward and others have done much to help newbies ever since (Tutorials, easier settings, quick start guide, etc).
I think its a great idea to use leo for your purpose, and I would start off by researching into the sphynx embedded in the documentation, which actually produces the leo website. There is a leo file containing it.
Anyway, thanks to clones and the easy scriptability, you will indeed be able to make most of the updating and editing automatic, just by properly arranging your nodes and using a bunch of menus/scripts.
I always try to give back and suggest scripts whenever my skill is suitable for the questions asked, and there is a very friendly community around which will always suggest the best way to fix your problems, at least that's what they did with me :)
Welcome, Davy!