Is craving unskilful because it fuels craving?

There are pleasures which cause no harm for others, do not require suffering of others to gain them, yet not in the sphere of the five senses.

Thinking that pleasure is bad, is foolish: no progress (going forth) without pleasure.

Short and hurtful for many or leaving the low realms of fight after not lasting.

If we say pleasure is bad, that would lead to the conclusion that one must practise extreme asceticism. The Buddha found that both extreme asceticism and extreme indulgence are both bad and prescribed the Middle Way through the Noble Eightfold Path.

If pleasure is not bad, then what is bad?

From SN 22.79:

"And why do you call it 'feeling'? Because it feels, thus it is called 'feeling.' What does it feel? It feels pleasure, it feels pain, it feels neither-pleasure-nor-pain. Because it feels, it is called feeling.

The feeling or experience of pleasure by itself is not bad. However, the passion for sensual pleasures, the craving for sensual pleasures and the clinging to sensual pleasures - that's what's bad in Buddhism. Not the feeling or experience of sensual pleasures.

From MN 75:

"Now suppose that there was a leper covered with sores & infections, devoured by worms, picking the scabs off the openings of his wounds with his nails, cauterizing his body over a pit of glowing embers. The more he cauterized his body over the pit of glowing embers, the more disgusting, foul-smelling, & putrid the openings of his wounds would become, and yet he would feel a modicum of enjoyment & satisfaction because of the itchiness of his wounds. In the same way, beings not free from passion for sensual pleasures — devoured by sensual craving, burning with sensual fever — indulge in sensual pleasures. The more they indulge in sensual pleasures, the more their sensual craving increases and the more they burn with sensual fever, and yet they feel a modicum of enjoyment & satisfaction dependent on the five strings of sensuality.

Sources of pleasure do not last forever. Sources of pain cannot be avoided forever. If somebody tries to take away your source of pleasure, you may feel angry. If someone tries to get the attention of someone you like, you may feel jealous. Clinging to sensual pleasures eventually lead to all the other negative states of mind. Clinging to sensual pleasures eventually leads to unsatisfactoriness and suffering.

From Itivuttaka 109:

This was said by the Blessed One, said by the Arahant, so I have heard: "Suppose a man was being carried along by the flow of a river, lovely & alluring. And then another man with good eyesight, standing on the bank, on seeing him would say: 'My good man, even though you are being carried along by the flow of a river, lovely & alluring, further down from here is a pool with waves & whirlpools, with monsters & demons. On reaching that pool you will suffer death or death-like pain.' Then the first man, on hearing the words of the second man, would make an effort with his hands & feet to go against the flow.

"I have given you this simile to illustrate a meaning. The meaning is this: the flow of the river stands for craving. Lovely & alluring stands for the six internal sense-media. The pool further down stands for the five lower fetters. The waves stand for anger & distress. The whirlpools stand for the five strings of sensuality. The monsters & demons stand for the opposite sex. Against the flow stands for renunciation. Making an effort with hands & feet stands for the arousing of persistence. The man with good eyesight standing on the bank stands for the Tathagata, worthy & rightly self-awakened."

But this does not mean that you must practice extreme asceticism. It simply means that we must try to eliminate the three poisons of passion / greed / lust, aversion / hatred and delusion. The goal in Buddhism is to experience sensations, and use them as far as they are useful, but not cling to them.

From AN 4.159:

Then Ven. Ananda approached the nun and, on arrival, sat down on a prepared seat. As he was sitting there, he said to the nun: "This body, sister, comes into being through food. And yet it is by relying on food that food is to be abandoned.

"'This body, sister, comes into being through food. And yet it is by relying on food that food is to be abandoned.' Thus was it said. And in reference to what was it said? There is the case, sister, where a monk, considering it thoughtfully, takes food — not playfully, nor for intoxication, nor for putting on bulk, nor for beautification — but simply for the survival & continuance of this body, for ending its afflictions, for the support of the holy life, [thinking,] 'Thus will I destroy old feelings [of hunger] and not create new feelings [from overeating]. I will maintain myself, be blameless, & live in comfort.' Then he eventually abandons food, having relied on food. 'This body, sister, comes into being through food. And yet it is by relying on food that food is to be abandoned.' Thus was it said, and in reference to this was it said.

Generally speaking, I think you're right.

Ānanda, when one dwells contemplating gratification in things that can be clung to, craving increases. With craving as condition, [the rest of D.O. chain] comes to be…. Such is the origin of this whole mass of suffering. (SN 12.52-57, 12.60)

In addition to that standard explanation that goes from enjoying to craving, Buddha also provides an alternative - when you enjoy and relish something, your mind "settles" in that...

Where there is fondness, relishing, & craving [...], consciousness settles there and grows. Where consciousness settles and grows, there is descent of name-&-form. Where there is descent of name-&-form, there is growth of tendencies. Where there is growth of tendencies, there is the production of renewed becoming in the future. Where there is the production of renewed becoming in the future, there is future birth, aging, & death, together, I tell you, with sorrow, affliction, & despair. (SN 12.64)

And in slightly different words:

Bhikkhus, when one dwells contemplating gratification in things that can fetter, there is a descent of consciousness. With consciousness as condition, name-and-form comes to be... [the rest of D.O. chain goes here] Such is the origin of this whole mass of suffering. (SN 12.59)

So, in my understanding, when you enjoy and relish something, your mind "settles" in that. When it settles, it takes something as a position, it assumes this is how things "are supposed to be". It then identifies with that position, "this is me, this is mine". Then from this position grow all kinds of problems, like:

• things change, you want to keep it the same but you can't - therefore you suffer.
• someone else found pleasure in some other experience, and settled in that - now their idea of how things are supposed to be is different from yours, so when you two get in conflict you fight - therefore both suffer.

So the problem with pleasure is this very "settling" of the mind, which takes its experience far too seriously and reifies it as absolute reality, "how things are supposed to be".

In Mahayana we say, you can experience pleasure as long as you see it as empty and therefore don't settle there. As long as you clearly see that the experiencer is a construct of mind, the experience is a construct of mind, the whole situation is a temporary arrangement, and the "pleasantness" of it is an illusion. When you see all that, you can still watch it, like when a grown-up watches a magic show where he knows all tricks. He can still kinda enjoy it - but not in the same naive way as kids do.

If he feels a pleasant feeling, he understands: ‘It is impermanent’; he understands: ‘It is not held to’; he understands: ‘It is not delighted in. [...] If he feels a pleasant feeling, he feels it detached; if he feels a painful feeling, he feels it detached; if he feels a neither-painful-nor-pleasant feeling, he feels it detached. (SN 12.51)

So, to answer your question, I don't think pleasure is only bad because it can't satisfy craving permanently, and if we look very carefully, I don't think we can say it is only bad because it fuels craving directly (although Buddha did speak about that too, as we can see above). Most importantly, from Buddha's explanations it seems that the big, "strategic" problem with pleasure is that it provides a comfortable ground for the samsaric mind of objectification and identification to grow on.

Now, you are asking, how is it possible for a non-Buddhist to realy appreciate this insight. I think the "tactical" part, about pleasure being unable to permanently satisfy craving and about pleasure increasing the craving, can be explained through the modern concept of addiction. You can say: "It is easy to get addicted to pleasure, but don't get addicted or else you'll want more and more, and will suffer when you can't get it".

The "strategic" part is harder to explain in modern language, or really in any language. Perhaps you could say, "Getting used to pleasure (really to anything "good") is dangerous, because first it becomes an anchor, then a reference point, then the center of your reality. And then you start measuring everything else against it, which determines your behavior. Then you're no longer shapeless and free, instead you are shaped and very vulnerable. Pleasure shapes you and makes your reality rigid. Once you have shape, you are mortal." - see, this part is hard to explain and hard to understand.