One thing I thought was missing from the post was, "Why can't you learn/reorganize the system yourself (or have someone else non-Bob do it)?"
It's the best of both worlds, keep Bob while having a functional system?
I've worked for a large NPO and change is very scary (not to mention the fact, electronic transmittal of confidential documents via the internet (ie. use of Google Docs) is commonly forbidden).
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One thing I thought was missing from the post was, "Why can't you learn/reorganize the system yourself (or have someone else non-Bob do it)?" It's the best of both worlds, keep Bob while having a functional system? I've worked for a large NPO and change is very scary (not to mention the fact, electronic transmittal of confidential documents via the internet (ie. use of Google Docs) is commonly forbidden).