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I think the teachings are fairly straightforward on the subject of Enlightenment and attachment to worldly (or indeed spiritual) experiences - they are fundamentally incompatible. And this is quite logical. To be attached and in any way dependent upon pleasures to be gained from the world is obviously a limitation. The true nature of the Self is unlimited. This obviously implies that if Alan Watts was attached to such things as wine, women and song, he couldn't have been enlightened.
Looking at it from the other side, if one is enlightened, there is no limitation at all.
Thus one is able to enjoy whatever comes along to the full without worrying about how soon it is going to come to an end, whether it can be prolonged or repeated etc., all of which must obviously restrict that enjoyment to some degree. There would be no attachment, no desire, no resentment, worries or reservations, just pure and total bliss - our natural state when it isn't covered over by our artificial nature and ignorance.
Furthermore, if/when one becomes enlightened, there is no need for any of these worldly things - one is all-bliss etc. already - there is nothing that any of those can give you. However, having 'become realised', the body will carry on doing the things it is used to doing, like a clockwork toy running down perhaps.
It has its so-called prArabdha karma and will work these out by law. (Once the gun has been fired, the bullet will travel to its target.) But the realised man also knows that he is in no sense the doer of actions. Before, he believed he was the clockwork toy in fully powered working order but thought that he was somehow in control. So, perhaps all of this describes Alan's position, namely that he had realised but was 'running down'?
No-one can ultimately know the answer, not even a realised man (since, being realised, he also now knows that there is no 'other' who is still not realised!).
Obviously I did not know him and most of what I know about him comes from what I have read on this list. It sounds as though, whilst being extremely knowledgeable on so many aspects of Eastern philosophy and being able to communicate these ideas so very well, he was nevertheless still unable to let go of some of the more worldly enjoyments. It does not seem reasonable that regularly getting falling-down drunk could be a working out of the remaining karma of a realised man. One also has the impression that much of the drive for sex is to achieve some sense of unity, if only for a few moments. A realised man knows that unity all of the time - what would be the point of seeking it through sex?
In respect of this last point, I recently read part of an excellent dialogue with Sri Poonja, in which he is asked "There are many paths to Enlightenment, including a path that uses union with a partner as a way to the Divine. Some people have experienced, when making love with their partner, a feeling of oneness with existence. Do you believe it is possible to achieve true liberation in such a way?". The response was "Physical activities can only produce physical results. Mental activities produce mental results. Sexual activity produces babies. Enlightenment is not produced by any of them."
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