Former hedonist started with Samatha, worried about dukkha nanas

You should never compare your personal path with others. Buddhism makes it very clear some people enter the Path and others do not. As Jesus said: "two men will be cultivating a field. One is taken away, the other is left behind" (Matthew 24:40-42).

It is best to avoid the ideas of "dark nights and dukkha nanas". Generally, these terms are used by individuals who wish to claim their mental illness is enlightenment or stream-entry.

The common arising of certain difficult existential emotions, such as "fear & dread", when one is practising solitude, are not any special "ñāṇa (insight knowledge)". While understanding such emotions are impermanent and understanding how to pass through them is a type of knowledge, this knowledge is not anything profound or special. It is merely understanding how to deal with a hindrance. Real insight knowledge results in a bliss, peace & freedom the ordinary person cannot even imagine can exist.

When the later day Buddhist literature refers to "bhaya ñana (knowledge of fear)", this does not refer to emotional fear but refers to the fearful nature of impermanent phenomena; that these impermanent phenomena will cause suffering if they are craved & attached to.

To see a beautiful woman and not having the instant image in your head of possessing her is not anything special. Instead, it is the most basic form of morality. Prior to the Cultural Marxist Sexual Revolution & its birth control of the 1960s, most men did not think of having sex with every beautiful woman they saw. Instead, most men understood with proper morality that marriage was the only place for sex.

Try to imagine you lived 70 or 100 years ago, when no women had the birth control pill. Do you think those women would have promiscuous sex? Do you think you yourself would entertain sexual thoughts without fear of causing pregnancy?

Have you not seen clearly all of the neurotic women in the current world, including beautiful ones? How can one even consider having sex with such neurotics and adding more harm to that which already exists?

In summary, what you are posting about are not "ñāṇa (insight knowledge)". About what is actually "right ñāṇa", the older scriptures describe a special knowledge that can only arise when a practitioner has developed right view, right thought, right speech, right action, right mindfulness, right concentration, etc:

Of those, right view is the forerunner. And how is right view the forerunner? In one of right view, right resolve comes into being. In one of right resolve, right speech comes into being. In one of right speech, right action... In one of right action, right livelihood... In one of right livelihood, right effort... In one of right effort, right mindfulness... In one of right mindfulness, right concentration... In one of right concentration, right knowledge... In one of right knowledge (sammā ñāṇa), right release comes into being. Thus the learner is endowed with eight factors and the arahant with ten.

MN 117

If you aspire to practice the Buddha's Noble Path:

1. You must learn the Noble Eightfold Path, quoted above. Notice how the Noble Path includes Right Resolve and Right Action, which includes the resolve to harmlessness, the resolve to not engage in harmful sexuality and the action of harmless sexual conduct (such as mutual commitment to marriage) or, otherwise, celibacy.

2. You must associate with Noble Friends who understand the Noble Path.

If the Noble Eightfold Path is practised as intended, the mind will become calm and, as concentration develops, the mind will become blissful, buoyant & radiant.

As for the blogger quote you posted, as I said at the beginning of my answer, meditation is not suitable for all people. Some people have engaged in too much bad kamma in the past and damaged their brain, thus meditation will take them straight to "hell", where they experience the results of their prior harmful deeds Some people have not developed enough sacrificial virtue, goodness & unselfishness to enable them to let go and be non-attached in meditation. Or some people are simply not genetically predisposed for the practise of meditation and their lust for life or self-survival instinct is too strong.

In conclusion, if your practise of Buddhism has brought good results for you, you should continue it. You should not compare yourself to others.

There is some truth to what this person wrote and I can imagine one can end up like he/she did but I don't think it is caused by meditation itself.

I read a sutta a while ago and I just can't seem to find it. The gist of it as I recall it was that a disciple of Buddha was accused of being hopeless and to not have faith in the Buddha. Asked by Buddha about it he affirms it and explains it as having attained equanimity and being absolutely certain that Buddha was right.

So the question is: Why is hopelessness a good thing?

All to many people never really become hopeless in the sense that they are indifferent. To most people hopelessness means not ever having a chance at getting/becoming what they want.

The hopelessness we are talking about is what can be experienced if you make your wildest dreams come true. Reaching the greenest pastures so to speak. In this moment I guess anybody would be overwhelmed by all the realizations this comes with. At first mostly disappointment. But later on lacking goals really starts to bug you. You always strived for something and now you know it is all worthless and a waste of time. What to do next?

At this stage there are two possibilities. One: find a new goal in search of fulfillment and the other: free yourself of this need. Sadly starting with meditation can be used for both. In the realization that material needs and outward sensations don't fulfill, some may try to "better" themselves. Become more than they are. But the thing is: You can't or at least not in this sense.

That is where this person is stuck. It became the new goal in life. It was supposed to add to him/her. In the end it didn't live up to this persons expectations which led to despair.

So back to hopelessness. What if in the end no state of the world would be superior to any other state? Wouldn't this mean freedom? So if nothing matters and there is nothing to lose why not go to town? That is why! You have nothing to gain either. You don't need to kill because the world won't become a better place without whatever being annoyes you. You don't need to steal because being richer won't do you any good. You don't have to lie and cheat because it won't do you any good. And with time it will lead to less hurt inflicted on you and people around you.

That is why if meditation is hard on you maybe try starting off with refraining from causing hurtful acts by keeping the Precepts. Less regret is always a good way to cultivate a clearer mind until maybe it won't be so hard to bear with.

What is the end game? Is it to become a mindless zombie?

The fully liberated ones (called arahants) do not experience any kind of mental suffering. They may experience physical pain which they endure and not suffer mentally from.

They do not have latent tendencies (anusaya), defilements (kilesa), effluents (asava), fetters (samyojana), the five hindrances (pañca nīvaraṇāni), craving (tanha), clinging (upadana) and the fourteen unwholesome mental factors from the Abhidhamma. They do not have the 3 poisons (greed/ lust, aversion and delusion).

They may plan to do something (see this answer), but they never plan to become something or somebody. They don't brood about the past or, dream or worry about the future.

Where the unenlightened feel boredom due to inactivity or feel loneliness due to lack of company, the arahants feel completely at ease and peaceful, and even prefer this. Their mental state is peaceful, free of "noise" and mental agitation of any kind.

They eat or take care of their health only out of necessity for maintenance and not with desires for sensual pleasures or to become something or somebody.

Each of the technical terms mentioned like fetters, hindrances, effluents, defilements, craving, clinging, unwholesome mental factors, 3 poisons etc. are all very detailed and often expand into further lists and definitions - you can search for them on Buddhism.SE.

But if you want a super short summary - it's bliss and peace all the time.

Also please see Dhammapada chapter 7.

Having studied theravadin canon and a lot of commentary i can advise you in short.

Don't overcomplicate your training by using non-canonical expressions like 'dark night' and 'insight knowledges'. These are commentarial developments and are controversial.

The way meditation is streamlined and made into a cookie-cutter method by ie the Goenka & Mahasi traditions, is a seemingly neat & convenient attempt at making a one size fit all and this one needs in order to train mass amounts of people with little to no instruction. However the theory as it is thus presented is at best incomplete and at worst a misinterpretation of the texts.

Basically both the Goenka and Mahasi traditions are rather niche traditions that became popular due to that massive streamlining of 'vipassana' and are based on commentary interpretations & systematizations on which there is little to no agreement.

Focus instead on studying the teacher's instruction and you will probably see that the method of expression is supreme and is optimized for the training such that no additional systems of going through insight knowledges and dark nights are required.

In no discourses of the Buddha will one read about a person resolving on or going through the insight knowledges & stages of insight, nor being instructed to do so.

The end point of practice is liberty: not the commonly-heard but overly simplistic notion pf political liberty, but the essential principle that underpins that concept. Unfortunately, this sense of metaphysical liberty can be deeply unnerving (heck, even political liberty can be unnerving). People like limits and boundaries, whether to hide behind or push up against; having limits and boundaries makes one feel safe, and gives one definition and identity.

The author of the post you quoted ran up against this issue, and had a negative abreaction. In effect, he went into the practice thinking that Buddhism would give him an identity and a purpose; that it would place safe and comfortable limits he could live within, and give him guidance forward. I imagine he (like many others in the West) adopted Buddhism because he felt resentments or anxieties about the world at large; he transferred his expectations from the world (which failed him) to Buddhism, thinking that would be the solution. But then when he started to run up against that openness (emptiness), his mind didn't know how to cope with it — it didn't know how to move without something solid to push against — so all those resentments and anxieties resurfaced and he transfer his expectations to something else, or perhaps just collapsed into defensive nihilism. At any rate, he conflated the practice with the purpose. The practice isn't liberty, the practice is how we come to understand liberty.

Dark moments come whenever the mind realizes it is not the master of something it thought it had in the bag; when it realizes that something it relies on isn't so simplistically reliable. One of the presumed boundaries of the world disappears, and it throws the mind off balance. C'est la vie... But when one has seen through all the boundaries, one lives in a perpetual state of balance.