I've found myself in similar predicaments. When it comes to governance, boards make decisions, not individuals. Directors must have enough respect for their fellow board members to be willing to hear differing opinions. Why should Bob hold so much power of the other directors? Is Bob really that bossy, or are the other directors really that insecure? Either way, the board should address this problem before anything else. If Bob is truly offended by a relevant suggestion, it is possible that unrealistic expectations were set when he joined the board. Or, perhaps he shouldn't be on the board in the first place.

Lastly, the points you make as to why the system should be abandoned could be indicators of other problems.

1. See point 4--if no one uses the system, no wonder there are out of date documents. Systems must be maintained.
2. Again, see point 4--if no one uses the system, no wonder it's disorganized. Systems must be maintained.
3. Why haven't the others taken an interest in learning how the system works?
4. Is this really accurate? Perhaps it's become a monster because no one uses it and Bob finds himself overwhelmed.

Perhaps all the members could use a lesson in cooperation. Has anyone spoken to Bob to see how he feels about the system? He may have designed it, but even he should be able to see its flaws. Perhaps Bob never got any input from anyone else who uses the system. Of course, that requires people to actually use the system in the first place. Perhaps Bob never got any input from the intended users before building the system. In my personal experience, I've learned not to invest a significant amount of time in a project unless it will help me, personally, or the folks it will benefit are actively involved in its creation. If it's not going to help me and no one else cares, why should I waste my time?

I heard she only visits once a month.

Who says Tux isn't female, or that Beastie isn't raping Linux as an expression of power, as opposed to sexual preference?