I know I've said this before both here and on the Foobiverse but I'll say it again: Michael is a hapless boob when it comes to money. No matter how much he and Deanna make, he will spend the rest of his life just barely scraping by. This is because he is not a citizen of the real world. Practicalities like saving for a rainy day, budgeting, investing for the future, paying off debts and his income tax and the like are an unwelcome restriction on his supposed freedom of action. This is why he spends money that would be better put aside for his family's future on lattes and bribes to parking lot attendants. This is also why he fled Portrait: it looked to him like Gluttson was using the issue of money to compromise his vision. The only reason this idiot isn't living in a cardboard box somewhere holding out a sign saying "I will be a pretentious snot for food" is that he lives off of his wife. Some masochistic impulse keeps Deanna loyal to the fool even though she must know that the only way he'd ever really pay his way is if she were to stage his death so that it looked like an accident. Hers is a 'love' that would endure even after the taxman came looking for his pound of flesh. She's willing to endure a frantic, threadbare existence of needless penury just to prove to her mother that she can't boss her around.