I think it's worth noting at this point that Michael Davies has been saying for at least a year that he is trying to launch all sorts of extensions of the Jeopardy brand - a nationwide tour of the Inside Jeopardy podcast, Jeopardy-branded bar trivia, etc..
There have been a handful of Inside Jeopardy Live events, but no nationwide tour. Jeopardy-branded bar trivia has yet to materialize.
Taking all that into account, and adding in all the points Joe, Brandon, and Kevin mentioned, I think a Jeopardy Live tour in the vein of TPIR Live or WOF Live is highly unlikely to happen.
On the other hand, the OP also mentioned PYL Live - that sounds to me like it would actually work, and I believe has been done on some cruise ships.