Penniless and Care Free
Grandpa Martin Vanderhof. The guy who puts the, "You can't take it with you" in You Can't Take It With You.
No really—he's the guy that actually says that line to Mr. Kirby.
Yup, he doesn't care about money or material things—you can't take them with you, after all. But he wasn't always a pseudo-hippie with a passion for family mayhem. He used to be an uptight suit, just like Kirby. But then one day—way before the start of the film—he just realized he wasn't happy:
"Then one morning, when I was going up in the elevator... it struck me I wasn't having any fun. So I came right down and never went back. Yes, sir. That was thirty-five years ago."
And ever since that time, Grandpa has done just what he wants — collecting stamps, sliding down banisters, and playing the harmonica.
The Sycamore household is Grandpa's house; everybody follows his path. No one works and everyone does as they pleases. Mrs. Sycamore writes, Essie dances, Ed prints; nobody really tries to make money… except for Alice, whose secretarial job seems to be mostly a hobby (she isn't concerned when she loses it).
Grandpa is in the business of spreading his gospel of indolence as well—as Mr. Kirby says, he sometimes sounds like he should be in the pulpit. Grandpa gets Poppins to quit his boring job adding up numbers in a real estate office by promising him space at the Sycamore pad to make his bunny toys. And, of course, he encourages Mr. Kirby not to work so hard either:
GRANDPA VANDERHOF: What if all your deals fall through? Might be a good thing for you.
MR. KIRBY: Man, you're crazy.
GRANDPA VANDERHOF Well, maybe I am, but I used to be just like you once. […]
This interaction really does have the ring of conversion to it—it's not that hard to imagine Grandpa saying "I used to be just like you once: a sinner!" instead of the implied "I used to be just like you—a greedy-guts!"
Work and money and jobs and worrying about bills and taxes—Grandpa shrugs them all off. If he needs anything, he trusts in God—and in his neighbors, who love him, and happily pay his $100 fine when he needs to get out of prison. Grandpa shows that if you have love, you don't need money. You just need, um, friends with money.
Wealthy and Care Free
Or, maybe, Grandpa shows something a little different. Because… is Grandpa actually penniless?
Sure, he doesn't work at a conventional job. But Alice mentions that he used to make a lot of money in his old job. He also assesses stamp collections, a job that Alice suggests is at least somewhat lucrative. He even owns his own house, which wouldn't have been all that common during the Depression.
In fact, it's because he owns the house that Mr. Kirby isn't able to buy up the entire block. Mr. Kirby's neighbors are protected, not by Grandpa's love and friendship, but by his money.
That's the case for all the people who live in Grandpa's house, too. Poppins is able to leave his job because Grandpa decides to support him. Similarly, Essie and Ed and DiPenna can do what they want because Grandpa houses and feeds them. Kolenkhov comes for dinner every night because he can get a free meal… but that free meal is available because Grandpa pays for it.
However, Grandpa keeps insisting that money doesn't matter:
GRANDPA VANDERHOF: Scum, are we? What makes you think you're such a superior human being? Your money? If you do, you're a dull-witted fool, Mr. Kirby. And a poor one at that. You're poorer than any of these people you call scum, because I'll guarantee at least they've got some friends. While you with your jungle and your long claws, as you call 'em, you'll wind up your miserable existence without anything you can call friend.
It's hard to argue with Grandpa's logic here: friends = good, being a miser = bad. But the truth of the matter is that Grandpa is able to become a generous, "superior human being" because he's able to be generous with… his money.
Sure, he may not be as wealthy as the Kirbys, but he's comfortable enough to support his child, his grandchildren, his in-laws, servants, and as many hangers-on as he likes. He can take life easy because he's well off. You can't take it with you—but if you want a fun life playing the harmonica like Grandpa, it's not a bad idea to have some of that money on you here, in this life, where it will do you some good.