I think he already has privately. His recent BlueSky rants and the fact that he changed his "age" last birthday from "21 forever" to "24 forever" plus Flutter seemingly "breaking up" with him (when she likely was never his girlfriend) and his whole "redemption arc" that he has recently started seem to be signs of a midlife crisis. He knows that he is likely more than halfway through life, possibly even two thirds. Remember Bob died at 84 and Chris is more than halfway to getting to that age while being considerably unhealthier than Bob was at his age (around 1971-72 when processed food was still pretty uncommon). Remember that Bob had him at 54, and probably had higher levels of testosterone than Chris does today (almost non-existent), despite him being a decade younger than that.
My conclusion is that he now looks back at the classic era (2007 - 2011) the same way that he looked back at high school back then: a better time with missed opportunities.