As for the future: I'm hoping this becomes a "thing" that Jesse does every year. Beyond that, I hope he runs more one-shots in general. I feel like he's always had the right stuff for GM-ing, he just needed the experience to be comfortable in the big seat.
Other thoughts: Tales from the Loop was the perfect game for Jesse to run. Zeke was a surprise casting as something of an outsider in Jesse's friend group, but ultimately he fit right in and added the right spice to the show - you can always rely on Zeke to dive in head-first with Rollplay.
I'm also expecting the sequel to this holiday special to follow a different dramatic "expectation" entirely, knowing Jesse... probably gonna be weirder and more in your head.