You can tell him this from another lawyer:

1. Leaving tracked changes on for a lot of editing is asking for trouble. It may be necessary, but make backups.
2. Every time a field updates, Word sees it as a change (even if the result is the same).
3. The option to update tracked fields before printing is causing at least some of the problem.

If he/she can remember:

• Before printing, save the document and turn off tracked changes.
• Update all fields.
• Print and close the document without saving.

I would recommend a versioning Add-In like Graham Mayor's save in two places.
Save in two places by Graham Mayor, MVP