If reincarnation is infinite, why haven't I reached enlightenment in a past life?

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You might have! Being a state of mind though, enlightenment doesn’t last any longer than your mind does. The soul (Atman) is eternal and unchanging. Our bodies come from the physical world, it’s development is influenced by our soul. So we are both material and soul-influenced. Once the body dies, the mind dies with it, and you progress through the heavenly realms using a spiritual body and mind until you’re ready for a new material existence at which point you’ll start the cycle all over again.

In an unfathomable way, my simple hypothesis is that we never experience the same thing the same way twice, we ‘carry over’ some stuff from one life to the next, what we call spiritual development. I have this worked out to have two components, level of consciousness and capacity for surrender. Enlightenment as Buddhists define it is a learned thing, you have to get educated about it and work to achieve the state, therefore developing both your level of consciousness and capacity for surrender in an accelerated fashion.

But then you die and you come back here and you have to do it all over again. This unfathomable-ness of exactly how individuals develop has been the ongoing subject of much much much debate over thousands of years. “Ultimate” moksha, where you just don’t reincarnate anymore, does not seem to be achievable to me in just one lifetime. I literally can’t even begin to imagine a being so pure and perfect that they’d literally have no further reason to incarnate in the material world. Even divine beings incarnate from time to time, most Hindu deities are not portrayed as having achieved liberation. Many schools incorporate a short period of very advanced enlightenment where one only reincarnates in heavenly realms until final moksha is achieved.

It’s best to think of the enlightenment that one achieves here as similar to other kinds of personal achievement / self development goals and stop the ‘all or nothing’ sort of mentality that only leads to more disappointment.