Burning or freezing, with cackles of frustration,
a night reclaimed and later days, self condemnation.
Twoson Hotel Businessman, Urban Zombie, and Dept. Store Spook
The Businessman in the Twoson Hotel will say seemingly random things if you repeatedly talk to him.
Burning or freezing,: He tells you "Is it cold today?" and "It's sooo hot today."
with cackles of frustration,: A "cackle" is a laugh with a harsh connotation. The Businessman tells you: "Ah! Hah Hahhhh..." and "You're annoying!"
a night reclaimed: If you continue to talk to him, he will eventually give you $50 "Here, get yourself a juice or something... *Ka-ching* (Ness got 50 dollars.)" $50 is also how much it costs to stay at the Twoson Hotel, so you had reclaimed the money you had spent to stay the night.
and later days,: Another quote he has is, "Later days, pal!" Incidentally Tomato also snuck this quote into the translated subtitles of a Dragonball DVD.
self condemnation.: Another (quite bizarre) quote he says is, "Dang me!"
There were some other great guesses like Brickroad and Starman Junior, but they didn't quite fit. Neither had "cackles" of frustration, and a "night reclaimed and later days" became a bit of a stretch. Excellent guessing regardless! After discussing it on the forum, I've also decided to accept Urban Zombie and Dept. Store Spook as well.