When reading the start thread I realize three things:
a) If I understand that correctly you want to keep Bob, but he is supposed to do it your way in future. So you don't suggest using Google Docs (this YOU and everyone else could do any time no matter if Bob goes along or not), you suggest Bob switches his system over to Google Docs. A monster that has grown for decades.
Well, even if I was convinced a new system in in order, if I had to do the conversion on a voluntarily basis because someone else said it is no good anymore ... good luck ....
I miss a little bit the "So I figured out how to convert the old files into google and am working on it because I believe the new system is so much better - and I hope Bob agrees when it is done or is willing to help me with that".
b) Before you have seen the new system work with the old data ... don't assume it will be better. Bob's system with a few files worked very well as I'm sure. If you've ever used Google Docs more extensively with larger files ... *cough cough* You basically make the same error, assumptions about the systems feasibility before having significant data imported and testing with these.
c) Personally I'd not touch Google Docs with a stick for anything I don't feel comfortable to be published for everyone and their dog to see. Clouds can be hacked and Google is a nice fat target. Google Docs is beta as any other system they have so the plug can be pulled any time. I'd suggest you look into a small but reliable personal webspace, set up a system a bit more sophisticated - there are people out there who actually know this kind of thing professionally and often are willing to help out for little money if the cause convinces them. ontact other non-profits for what they use etc, get something out of the box developed for the specific application you need, have your dedicated space (few bucks per month with hostgator or such), run regular backups.