Re: Rashi's weird genealogy
If you need advice about ancestry tree software please ask.
We (my wife and myself) also started out by paper and pencil, but to maintain a sizeable tree on paper is awkward, to say the least.
Also if you start early on by computer, it is very easy to put it later on the web, or to print copies for your relatives, from whom you wish to have additional information.
If you want to look at our family tree it is at:
(We have about 1500 names)
I don't suppose you have Hebrew, otherwise I would suggest to you to join our genealogy forum.