Yep, been there and done that but I made it a point not to have the bastard in my party ever again. I'm always anxious when someone unexpectedly (or as a matter of reciprocation) picks up a tab because I want to be sure the tip is generous. In fact, I often will insist on picking up the tip if someone else is paying the bill.
Regarding number 1 - lump sum at the end? I typically will throw down $5 every morning after a night's stay for routine service. I'll up it if they do something extra like turn my towel into a piece of art, leave extra coffee, or whatever.
You're talking pizza actually made in NYC - not just the NY "style" and not Albany, NY... NYC pizza, right? Because if you are, you have an affliction and I feel bad for you. Or you did it completely wrong. Brick oven, super-heated to > 800F, cooks in a few minutes... ain't a thing floppy about it.
I almost always stay at the Springhill Suites, less than 1.5 miles from the Shoe. There are a surprising number of spots to eat / drink a short walk from that hotel. But I typically stroll over to the Short North area to inflict maximum damage to myself.
NY has the superior pizza. Chicago has the superior hotdogs. These are irrefutable statements of fact.
I mean, that's just crazy talk. Deep dish sucks, so you can have the Chicago comparison. But compared to NY (especially Brooklyn), it's not even a sensible debate. I grew up eating pizza in Ohio, and I've had pizza in Columbus in the last couple of years when in town for a game. When drunk and hungry, it's just fine. I mean, I'm not choking it down; it's perfectly ok. NY is an entirely different animal. I go out of my way to have pizza in NY; it's fucking delicious.