I'm not familiar with the term "Jesting Pilate" (though I just googled it
and see that it is indeed a thing). I've always pictured him saying it
in a more exasperated way, kind of "what's truth got to to with it". He
seems to find no fault with Jesus but instead gives in to the braying
mob, and I think he's saying "well guilty or not he'll hang for it" just
to appease the mob.
So I don't think he's addressing whether Jesus' guilt is true or not, but
that he's going to go with the flow in any case. I don't therefore think
it's addressing the questions as to whether topics such as Dives and
Lazarus are literally "true" or not.