I feel like George, due to his cheapness, would have the most paper thin pillow in the world and he would have constant neck or sleeping issues because of it.
I think it'd more be Elaine trying to convince George that he needs more than one pillow and he'd insist it's fine and really dig in on the issue.
Then, at some point, Elaine has a possible buyer lined up and George has agreed to help her out.
While there, he lays on her bed to try out the pillows and passes out for hours.
He completely misses the guy who was going to buy it and gets lucky that the guy doesn't message Elaine anything. So George claims the guy never showed up.
Elaine angrily remarks, "Well, screw that guy for wasting your time--I'm gonna text him a piece of my mind"
George, frantically, "Oh, no no no no--you don't want to do that, Elaine"
E- "Why not?"
G- "Well, uhh, what if he had a family emergency and he wants the bed later or something? Probably best to not upset him"
E- "Oh. Ok. Good point."

George then goes down a path of scaring off anyone who wants to buy her bed by making up various stories when they look at it.
Eventually--he's so desperate for a nap that he poses as someone online who claims to be interested in buying it.
Elaine comes home early and catches George sleeping her bed with all sorts of relaxation music going and he's even wearing her sleeping mask.