Where does 'contentment' fit in walking the path of Dhamma?

In my humble view, the factor of Right Effort might address this question: The Buddha doesn't say, "Don't make an effort, be content," but rather the Buddha says, "Make an effort towards the right things." In SN 45:8 the Buddha explains that there are four things that deserve a monk's effort:

And what, monks, is right effort? (i) There is the case where a monk generates desire, endeavors, activates persistence, upholds & exerts his intent for the sake of the non-arising of evil, unskillful qualities that have not yet arisen. (ii) He generates desire, endeavors, activates persistence, upholds & exerts his intent for the sake of the abandoning of evil, unskillful qualities that have arisen. (iii) He generates desire, endeavors, activates persistence, upholds & exerts his intent for the sake of the arising of skillful qualities that have not yet arisen. (iv) He generates desire, endeavors, activates persistence, upholds & exerts his intent for the maintenance, non-confusion, increase, plenitude, development, & culmination of skillful qualities that have arisen. This, monks, is called right effort.

So as with many other things in the teachings, it seems to be more about asking oneself, "Will this lead to progress in the path?"

Metta.

One has to find contentment in striving.

Here and beyond he suffers. The wrong-doer suffers both ways. He suffers and is tormented to see his own depraved behaviour.

Here and beyond he is glad. The doer of good is glad both ways. He is glad and rejoices to see his own good deeds - Dhp

Monks, there are these four modes of practice. Which four? Painful practice with slow intuition, painful practice with quick intuition, pleasant practice with slow intuition, & pleasant practice with quick intuition.

"And which is painful practice with slow intuition? There is the case where a monk remains focused on unattractiveness with regard to the body, percipient of loathsomeness with regard to food, percipient of non-delight with regard to the entire world, (and) focused on inconstancy with regard to all fabrications. The perception of death is well established within him. He dwells in dependence on the five strengths of a learner — strength of conviction, strength of conscience, strength of concern, strength of persistence, & strength of discernment — but these five faculties of his — the faculty of conviction, the faculty of persistence, the faculty of mindfulness, the faculty of concentration, the faculty of discernment — appear weakly. Because of their weakness, he attains only slowly the immediacy [1] that leads to the ending of the effluents. This is called painful practice with slow intuition.

"And which is painful practice with quick intuition? There is the case where a monk remains focused on unattractiveness with regard to the body, percipient of loathsomeness with regard to food, percipient of non-delight with regard to the entire world, (and) focused on inconstancy with regard to all fabrications. The perception of death is well established within him. He dwells in dependence on these five strengths of a learner — strength of conviction, strength of conscience, strength of concern, strength of persistence, & strength of discernment — and these five faculties of his — the faculty of conviction, the faculty of persistence, the faculty of mindfulness, the faculty of concentration, the faculty of discernment — appear intensely. Because of their intensity, he attains quickly the immediacy that leads to the ending of the effluents. This is called painful practice with quick intuition.

"And which is pleasant practice with slow intuition? There is the case where a monk — quite secluded from sensuality, secluded from unskillful qualities — enters & remains in the first jhana: rapture & pleasure born of seclusion, accompanied by directed thought & evaluation. With the stilling of directed thoughts & evaluations, he enters & remains in the second jhana: rapture & pleasure born of concentration, unification of awareness free from directed thought & evaluation — internal assurance. With the fading of rapture he remains equanimous, mindful, & alert, and senses pleasure with the body. He enters & remains in the third jhana, of which the noble ones declare, 'Equanimous & mindful, he has a pleasant abiding.' With the abandoning of pleasure & pain — as with the earlier disappearance of joy & distress — he enters & remains in the fourth jhana: purity of equanimity & mindfulness, neither pleasure nor pain. He dwells in dependence on these five strengths of a learner — strength of conviction, strength of conscience, strength of concern, strength of persistence, & strength of discernment — but these five faculties of his — the faculty of conviction, the faculty of persistence, the faculty of mindfulness, the faculty of concentration, the faculty of discernment — appear weakly. Because of their weakness, he attains only slowly the immediacy that leads to the ending of the effluents. This is called pleasant practice with slow intuition. [2]

"And which is pleasant practice with quick intuition? There is the case where a monk — quite secluded from sensuality, secluded from unskillful qualities — enters & remains in the first jhana: rapture & pleasure born of seclusion, accompanied by directed thought & evaluation. With the stilling of directed thoughts & evaluations, he enters & remains in the second jhana: rapture & pleasure born of concentration, unification of awareness free from directed thought & evaluation — internal assurance. With the fading of rapture he remains equanimous, mindful, & alert, and senses pleasure with the body. He enters & remains in the third jhana, of which the noble ones declare, 'Equanimous & mindful, he has a pleasant abiding.' With the abandoning of pleasure & pain — as with the earlier disappearance of joy & distress — he enters & remains in the fourth jhana: purity of equanimity & mindfulness, neither pleasure nor pain. He dwells in dependence on these five strengths of a learner — strength of conviction, strength of conscience, strength of concern, strength of persistence, & strength of discernment — and these five faculties of his — the faculty of conviction, the faculty of persistence, the faculty of mindfulness, the faculty of concentration, the faculty of discernment — appear intensely. Because of their intensity, he attains quickly the immediacy that leads to the ending of the effluents. This is called pleasant practice with quick intuition.

"These are the four modes of practice. https://www.accesstoinsight.org/tipitaka/an/an04/an04.163.than.html

The Blessed One said, "And how, Nandiya, does a disciple of the noble ones live heedlessly? There is the case where a disciple of the noble ones is endowed with verified confidence in the Awakened One: 'Indeed, the Blessed One is worthy and rightly self-awakened, consummate in knowledge & conduct, well-gone, an expert with regard to the world, unexcelled as a trainer for those people fit to be tamed, the Teacher of divine & human beings, awakened, blessed.' Content with that verified confidence in the Awakened One, he does not exert himself further in solitude by day or seclusion by night. For him, living thus heedlessly, there is no joy. There being no joy, there is no rapture. There being no rapture, there is no serenity. There being no serenity, he dwells in pain. When pained, the mind does not become centered. When the mind is uncentered, phenomena do not become manifest. When phenomena are not manifest, he is reckoned simply as one who dwells heedlessly https://www.accesstoinsight.org/tipitaka/sn/sn55/sn55.040.than.html

Contentment is among 10 suitable topics for conversation

"Endowed with five qualities, a monk pursuing mindfulness of breathing will in no long time penetrate the Unprovoked [release]. Which five? ... "He gets to hear at will, easily & without difficulty, talk that is truly sobering & conducive to the opening of awareness: talk on modesty, contentment, seclusion, non-entanglement, arousing persistence, virtue, concentration, discernment, release, and the knowledge & vision of release. https://www.accesstoinsight.org/tipitaka/an/an05/an05.097.than.html

From dhp

Health is the supreme possession. Contentment is the supreme wealth. A trustworthy friend is the supreme relation. Nirvana is the supreme happiness

It is good to have companions when occasion arises, and it is good to be contented with whatever comes. Merit is good at the close of life, and the elimination of all suffering is good.

Restrained of hand, restrained of foot, restrained of speech and restrained in his highest faculty, with his joy turned inwards, his mind still, alone and contented - that is what they call a bhikkhu

Whenever he meditates on the rise and fall of the constituent elements of existence, he experiences joy and rapture. It is immortality for men of discrimination.

Therefore in this religion, this is what comes first for a wise bhikkhu - guarding of the senses, contentment, and discipline in accordance with the rules of the Order. He should cultivate friends of good character, of pure behaviour and resolute. He should be friendly in his manner, and well-behaved. As a result he will experience great joy, and put an end to suffering.

• I'm not sure what the Pali word for "contentment" might be -- perhaps there are several, with different shades of meaning -- the first I heard of was sukha

  Sukha (Sanskrit, Pali; Devanagari: सुख) means happiness, pleasure, ease, joy or bliss, in Sanskrit and Pali. Among the early scriptures, 'sukha' is set up as a contrast to 'preya' (प्रेय) meaning a transient pleasure, whereas the pleasure of 'sukha' has an authentic state happiness within a being that is lasting. In the Pāli Canon, the term is used in the context of describing laic pursuits, meditative absorptions, and intra-psychic phenomena.

• If you search this site -- https://buddhism.stackexchange.com/search?q=sukha -- you'll find several related posts; including for example, What are the differences between joy (piti), bliss (sukha) and peace (santi) and how do the qualities relate to Nibbana?

• At least one of these words -- pāmojja (translated "joy") -- is described as instrumental in Kimatthiyasutta (AN 11.1), which says that it's the purpose of "skillful ethics" and thence "having no regrets", and that in turns its purpose is rapture and thence tranquility (piti and passadi) and so on.

  I asked a question related to that sutta, here -- What is the basis? -- with a nice answer.

• I think of "content with little" as a description of an ideal or successful monk; but when I search for that phrase I find hardly any reference for it.

  The sutta mentioned previously seemed to be based on or arising from "skilful ethics" -- not possessions -- not "what you have", but perhaps something more like, "what you do or don't do".

• Your saying "walking the path" reminds me of this quote:

  Achaan Chah just laughed and pointed out how much the monk was suffering by trying to judge others around him. Then he explained that his way of teaching is very simple: "It is as though I see people walking down a road I know well. To them the way may be unclear. I look up and see someone about to fall into a ditch on the right-hand side of the road, so I call out to him, 'Go left, go left' Similarly, if I see another person about to fall into a ditch on the left, I call out, 'Go right, go right!' That is the extent of my teaching. Whatever extreme you get caught in, whatever you get attached to, I say, 'Let go of that too.' Let go on the left, let go on the right. Come back to the center, and you will arrive at the true Dharma."

  I think that "Middle Way", incidentally, implies "avoiding both extremes".

  I doubt that means avoiding every extreme or effort, though -- if you're not steering towards a ditch on the left or the right, then perhaps (I don't know) you're free to progress forward in a semi-unrestrained way. This answer for example talks about billionaires -- and mentions Anathapindika.

  Or from the Zen tradition there's the story of Publishing the Sutras -- which I find remarkable, both for the magnitude of the gifts, but also as examples of attachment or intention (dedication towards a goal) and of non-attachment (adapting to circumstance and letting go of wealth).

• There's a sutta -- Brahmana Sutta (SN 51.15) -- which addresses the apparent paradox of an intention to end desire.

  The word for "arrived at the park" there is ārāmagatassa incidentally; I see "ārāma" as a synonym for "a (forest) monastery" and so more generally "seclusion" or "the monk's life", and "gata" of course as reminiscent of "Tathagata".

  Also, on the subject of desire, Difference between desire (chanda) and craving (tanha)?

• Another sutta -- An 2.5 -- specifically emphasises (continuing) Right Effort even over any contentment associated with skilful qualities:

  Mendicants, I have learned these two things for myself—to never be content with skillful qualities, and to never stop trying.

  I never stopped trying, thinking: ‘Gladly, let only skin, sinews, and bones remain! Let the flesh and blood waste away in my body! I will not stop trying until I have achieved what is possible by human strength, energy, and vigor.’

  It was by diligence that I achieved awakening, and by diligence that I achieved the supreme sanctuary.

The sutta SN 16.1 is about contentment.

From SN 16.1:

At Savatthī. “Bhikkhus, this Kassapa is content with any kind of robe, and he speaks in praise of contentment with any kind of robe, and he does not engage in a wrong search, in what is improper, for the sake of a robe. If he does not get a robe he is not agitated, and if he gets one he uses it without being tied to it, uninfatuated with it, not blindly absorbed in it, seeing the danger in it, understanding the escape.

“Bhikkhus, this Kassapa is content with any kind of almsfood … with any kind of lodging … with any kind of medicinal requisites … and if he gets them he uses them without being tied to them, uninfatuated with them, not blindly absorbed in them, seeing the danger in them, understanding the escape.

“Therefore, bhikkhus, you should train yourselves thus: ‘We will be content with any kind of robe, and we will speak in praise of contentment with any kind of robe, and we will not engage in a wrong search, in what is improper, for the sake of a robe. If we do not get a robe we will not be agitated, and if we get one we will use it without being tied to it, uninfatuated with it, not blindly absorbed in it, seeing the danger in it, understanding the escape.

“‘We will be content with any kind of almsfood … with any kind of lodging … with any kind of medicinal requisites … and if we get them we will use them without being tied to them, uninfatuated with them, not blindly absorbed in them, seeing the danger in them, understanding the escape.’ Thus should you train yourselves.

“Bhikkhus, I will exhort you by the example of Kassapa or one who is similar to Kassapa. Being exhorted, you should practise accordingly.”

Also AN 6.114:

“Mendicants, there are these three things. What three? Lack of contentment, lack of situational awareness, and having many wishes. These are the three things. To give up these three things you should develop three things. What three? You should develop contentment to give up lack of contentment, situational awareness to give up lack of situational awareness, and having few wishes to give up having many wishes. These are the three things you should develop to give up those three things.”