illustration (attribution, if any possible, is at the end of the article)
Like other wholesome qualities, generosity, or dāna, may only become a pāramī / pāramitā (Perfected Quality) when associated with Wisdom, or paññā.
There's for example little 'perfection' (or constructive / wholesome appropriateness) in giving beyond one's means, falling into debt, being unable to repay, and creating stress and conflicts out of this causal chain.
Most people can give a small percentage of their resources. Most routinely do so, in fact, for the benefit of their "loved ones" or family… and they could do so for extended family, community or even a philanthropic cause, without noticeably changing their lifestyle!
The ordinary experience though is that, the further 'away' from the self the beneficiary seems, the harder it seems to muster the small contribution… but this clearly is based on mental fabrications (arbitrary distinctions and appropriations — mine vs. not mine): regardless of whoever benefits from it, the 'sacrifice' or 'restraint' is the same, isn't it? Unless it's not a generous act at all, but merely a manipulative scheme toward a future reward (e.g. via a 'moral debt' or a 'guilt' tripping)!
While Wisdom naturally seems included in the eightfold path (as the paññā subgroup: right view, right intention), many practitioners struggle to see where Generosity stands. As a result, they don't particularly make its cultivation a priority.
Being confused doesn't imply though that Generosity is a 'lesser' Perfected Quality when compared to Wisdom. It is noticeable that Generosity is consistently listed as the first Perfected Quality, be it among the 10 Theravāda pāramī (Wisdom is 4th), the 6 Mahāyāna pāramitā (Wisdom is 6th) or the 10 Mahāyāna bhūmi (Wisdom is 6th).
In relation to the eightfold path, Generosity could of course be a 'positive' counterpart of the "do not take what is not given / do not steal" declination of "right action."
It could also be the 'positive' counterpart of the "do not harm" perspective on the whole śīla subgroup (right speech, right action, right livelihood).
But one could argue that Generosity is the first pāramī / pāramitā because of its relation to "right mindfulness" (itself the main key to insight, and thus to Liberation).
As we've seen, giving is an opportunity to be mindful of one's mental fabrications and appropriations as well as of one's intentions. Such application of mindfulness certainly helps cultivating "right view" and "right intention", but repeated application of mindfulness is itself a cultivation of "right mindfulness". It's like going to the gym to strengthen a muscle and to embody constructive habits.
By supporting the cultivation of mindfulness, generosity constitutes a Dharma gate.
Most people (notably in rich countries, but elsewhere too) waste several percents of their consumption (food, electricity, car petrol, etc.) by not being mindful (e.g. of twisted priorities). If one takes 'consumption' in a larger sense, most people waste time too.
Part of the value in cultivating dāna is from the mindfulness it supports, a mindfulness transforming waste into wholesome resources: by paying closer attention to what one does and to how one allocates available resources, the minimisation of waste not only helps the environment (for the benefit of all sentient beings) but it also frees resources at no cost other than attention (resources which can then be given, rather than hoarded).
By relying on mindfulness, wise generosity based on the minimisation of waste therefore constitutes a Dharma gate.
[Sometimes giving the attention (and some time) directly to someone suffering from loneliness is all it takes!]
Being mindful about how the resources made available will be used (i.e. "mindful giving") constitutes another Dharma gate.
Ideally, the energy is spent in evidence-backed, cost-effective ways capable of effectively using more resources (be it funding, time or skills…). Sometimes, it may make sense however to take advantage of one's specific knowledge of a rarer opportunity, to "fund what others won't" (note: specific 'knowledge', not mere 'preference').
By asking the giver to enquire into its biases, preferences and prejudices (e.g. when reviewing the evidence) and by asking the giver not to limit oneself to what is 'habitual' or the social norm (e.g. when reviewing opportunities others might not fund), "mindful giving" supports mindfulness, which supports insight, so it constitutes a Dharma gate.
It was said the true Dharma is « good in the beginning, in the middle and at the end. »
Then, is it really a surprise that the cultivation of Generosity —which supports mindfulness in the beginning (enquiring into one's mental fabrications and intentions), in the middle (freeing resources) and in the end (deciding on the allocation)— might indeed deserve the first mention among Perfected Qualities?