It's a really hard thing to do, isn't it! I was in a similar situation - with the company for 6 years, handled the technical and sys-ad aspects of the studio and knew stuff that nobody else did. The difference for me was that I left entirely instead of taking maternity leave, as we moved interstate when I was six months pregnant.
I wrote a detailed procedures manual (over 50pages) which gave step by step instructions of how, why and when everything should be done. I also had six weeks to train my replacement. I had a systematic plan in place of training him so that by the time I left he was able to do the majority of things that I did, and knew enough to be able to find out about the things that he didn't know. Six weeks was not enough time to teach somebody a job that had evolved over six years, so I prioritised and taught him the most essential things, especially those tasks that definitely couldn't be delegated to somebody with more experience (eg: my bosses).
It was really hard to let go, especially as I knew that I could do a better job in a fraction of the time, and I did get some frankly ridiculous questions in the first few months after I left, but now I only get the occasional question. It was a bit hard to realise that they really could cope without me (LOL), but I consoled myself with the knowledge that they too found it hard to see me go, and they still consider me a valuable asset to the company. I am still in touch with the two owners - who are like family now - and we are talking about me undertaking projects which I can work from at home.
I'm not sure if anything I've said is of any help - it's more of a ramble really - I too was unable to answer the question of how to make them self sufficient without feeling left out - kinda like raising kids really!
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