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Does wise practice of compassion ever lead to suffering or bliss for the practitioner?

Is there a difference between compassion cultivated through the Brammaviharas and compassion cultivated through Vipassana insight?

If one is enlightened does that mean one is compassionate or fully compassionate?

Why does wisdom lead to compassion or compassion lead to wisdom?

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Yes, there is. There is a difference between compassion cultivated through the Brammaviharas and compassion cultivated through Vipassana.

With the Brammaviharas, one can be as compassionate to the maximum, but that does not mean one has gotten rid of ignorance. Those beings in the Brahma worlds do not generate any hateful thoughts. They have perfected the four Brahmavihara of metta, karuna, mudita, & upekkha. Yet they have ignorance (moha), even though they don’t have a trace of hateful thoughts, and thus can be reborn in the four lower realms.

Even if one gets rid of greed and hate, will still have ignorance, and will end up getting back greed and hate due to ignorance. But when compassion is cultivated through Vipassana, wisdom, or panna arises. The Buddhist mental factor ‘Adosa’ is not mere absence of ‘dosa’, but embodies compassion. The more panna one has, it is more likely that one would be generating ‘adosha’ and ‘amoha’ thoughts of compassion more often.

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You can practice Brahmaviharas where the unwholesome roots remain dormant. This is by means of suppression or certain thoughts and replacing them with positive thoughts which might be through verbalisation. When you suppress it may bounce back with a vengeance when your concentration breaks.

When you practice Vipassana you are removing the defilements from the root. This way Brahmaviharas can be developed with more depth and stability.

Neither way is suffering through the effort you apply may not always be viewed as pleasant.

Compassion and wisdom goes hand in hand as mentioned before. One contributes to the other.

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To answer your 4th question, wisdom is knowledge of truth, and compassion is acting in accordance with that knowledge.

I can search for this in the suttas, but not sure that it will be explained as such. It is just what the words mean.

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Does wise practice of compassion ever lead to suffering or bliss for the practitioner?

Perhaps indirectly: compassion with attachment (or with conceit) could lead to suffering; conversely though, a skillful act of compassion might be occasion for lack of remorse, and so on.

Is there a difference between compassion cultivated through the Brammaviharas and compassion cultivated through Vipassana insight?

I don't think of Vipassana as a "cultivation" (a Bhavana).

Perhaps Vipassana leads to compassion by taking away obstacles (e.g. seeing without selfishness or without clinging), whereas cultivation (karuna resulting from metta-bhavana) is by adding incentives or motivation (e.g. viewing other beings as if they were your own friends and family).

If one is enlightened does that mean one is compassionate or fully compassionate?

I think that's a difference between different traditional categories of enlightenment: e.g. arhats and private-Buddhas are less well-known for their compassion; conversely the compassion of a Boddhisatva or Buddha is more famous (or more effective, more evident).

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Does wise practice of compassion ever lead to suffering or bliss for the practitioner?

Yes, the Brahmavihar compassion is meant as an antidote for jealousy and feeling of being rejected/wronged by the world. Generating compassion puts one into an elevated position, so one can feel better.

Is there a difference between compassion cultivated through the Brammaviharas and compassion cultivated through Vipassana insight?

The realization-induced compassion is spontaneous and more authentic than the generated.

If one is enlightened does that mean one is compassionate or fully compassionate?

Perfectly compassionate. Which among other things means that one sees Samsara as Nirvana.

Why does wisdom lead to compassion or compassion lead to wisdom?

Wisdom leads to compassion, because we clearly see how foolish people suffer from self-inflicted trouble. We see how they entangle themselves in difficult karma due to pointless goals they saw as important. We see how people expect things to last despite the impermanence.

Compassion leads to wisdom, because it's a practice that helps one detach from the egoistic concerns, disentangle, and achieve enlightenment.

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