As always, save scumming is good to make sure you win checks. If you keep Locke on your roster, he increases obedience more than you lose it typically. Felicity does the same for comfort. If you are still low on obedience, you can go to the table for managing the house and do obedience training until it gets up. As far as money, try to get the Thief cat and they will keep your money up. Keep in mind that everyone works worse when you are already low on obedience. You can also get money from town.