Right off the bat, it's obvious to everyone who isn't Phil or John that we find ourselves dealing with a false dilemma. It's clear that Phil thinks that hiring a moving van like a sensible person is somehow a very bad thing indeed because he has to pay someone to move his things for him and somehow feel himself to be less of a man. This, I should think, is why people prioritize beating the garbage man over weddings and it's why people mow lawns when other people are pressed for time.
This leads us to the next point of failure: the unswerving belief that he's somehow beating the system and keeping someone from doing him injury. Just as John applauds himself for his cleverness in finding a dumpster to keep from being humiliated by a phantom enemy and as he will try really hard to think that Elly wants to spend him into poverty with her crazy request for a new kitchen, Phil clearly thinks that he's fended off his wife's attempt to castrate him.
What he's actually done is something far more depressing: he's cut off his nose to spite his face because the money-saving masterstroke is more expensive than doing things right and also manages to horribly inconvenience Georgia. Instead of having the peace of mind of having his belongings in a nice, comfy van that isn't exposed to the elements and a wife who isn't asked to save him from his own stupidity, he has to worry about water damage and the fact that for some reason that can't possibly be that his 'free' van costs too damned much, Georgia wants to kill his stupid ass.
Finally, we get to the point of things: his failure to learn from his mistake because doing so would, of course, lead to his being humiliated and made less of a man. If the people who tell him that he's headed for a fall are right, his illusion of having common sense goes away and that would revert him to the status of a child telling his mother that no, he doesn't know what's good for him. This means that inside every dumb-ass 'beating the system', there's a mopey little kid dreading eating his spinach like he's supposed to.