I don't think all taxes are legalised theft. Consider a sales/consumption tax: I think one could make a valid argument that it's a charge by the state for doing business in their area - a charge that helps pay for the various services (eg, police, sanitation, transport, etc.) that the state provides so that the environment is friendly for commerce. If you feel that the charge by the state is too large, you are free to go to another area to pay less taxes but also suffer the risks of that state (for example, Pakistan has lower taxes than the US but also fewer services)

I think a similar parallel exists for income and capital gains taxes (where the government takes a cut of what you earn) - it's a charge for use of all the services that the state provides to make the area useful to work in.

If you're claiming that mechanism is 'theft', I think many other items become theft: if I allow someone to run their business out of my office for 10% of their revenue, is that theft? I would consider that a form of rent. Is it just theft when it's done by the government?

Just a few quick possibilities:

1) You could try the 'duplicate, don't replace' strategy. For instance, minutes of the board meetings go in Google Docs (so they can be searched more easily) and then are copied over to Bob's system once approved. If you do it right, eventually Google docs will start to become the primary source system - simply because it's easier to use - but Bob will still be maintaining his system. The downside to this is that you'll have a lot of documents in two places but eventually you can drop the one that isn't working.

2) You try to give Bob some kind of new, very cool project for him to work on - that is, give him a way cooler, more interesting bone and maybe he'll drop the one he's got. How's your donor database? Do you need some kind of app built for mobile or something? Once he's up and handling that (and gotten some real street cred for a good project), you might be able to obsolete the document management thing.

3) Work on a Business Continuity Plan: an early step in all BCP's is to make sure that you can (a) recover the documents if disaster hits and (b) that no one person is a single point of failure. Use the recent 'Sandy' events to emphasize that this is not a slur against Bob but the organization has to be able to survive even if the current 'datacenter' (even if it's just a machine under a desk) is flooded/destroyed. Google Docs is far cheaper from a recovery point of view.

4) Emphasize the shared document approach to Google Docs - if you have remote meetings, it's much easier to use Google docs to share/edit and remotely collaborate. Again, merging with approach #1 (use Google Docs until it's finalized, then it goes into the Bob system) might work well.

Good luck.

I've seen a lot of folks suggesting that you focus on documenting but I take the opposite view: you should actually be working to make documentation unnecessary. Documentation, by its very nature, tends to become obsolete very quickly - and any good IT guy learns to look at what's actually going on in the system rather than relying solely on the documentation. So you want to make your system as self-documenting as possible:

• Set up a good monitoring system - that's a great starting point for your successor because he can deduce what's important by what's being monitored. Get someone else to be involved in monitoring (maybe your boss?) and you've got a second person who knows what is important.
• Use a good naming convention - EmailServer1, TelephoneCloset3 are good names. Ninja, Macbeth, Comp1, etc. are bad.
• Fix DNS so that common names go the right place - typing 'wiki' into the browser should go to the wiki, 'monitoring' should go to the monitoring system, etc.
• Never build machines manually - Use configuration management software, automate builds, make them as push-button as possible.
• Use an web/online Task List - Get in the habit of using task list software (I like PivotalTracker, personally) Giving your successor a list of what you worked on over the last month is really useful. Plus, it's an easy way to sit down with your management and show them what you'll be working on over the next week/month/year.
• Automate those simple tasks you do all the time - Do you find yourself clearing disk space? Running reports? Run them from your management/monitoring console instead - that way, there's at least a script for someone else to read.
• Finally, set up a wiki to document anything that isn't covered above - there will always be something but hopefully it will be a short list.

I've done this three or four times and it's worked every time.