The Chronic Reincarnator TCR

It's been over two thousand years of consecutive lives for the protagonist, at this point it's safe to say they've gone past depression and into the inescapable cynical void.

In an unusual turn of evens the protagonist is reborn again but this time not as a baby, but as an eight-year-old - furthermore they discovered they not only reincarnated as a different gender for the first time in the above mentioned two thousand years - luckily for the protagonist, a certain someone offers them a deal, survive till the end this one time and get a way out of the cycle of reincarnation.