The second Win is that Paul's wife is pretty hot in the movie. We also know that they had intercourse at least twice due to the presence of 2 daughters. This proves he could either afford in vitro, which is highly unlikely given his financial woes at the beginning, or it proves that his marriage was, inexplicably, for love. Intercourse supplies the third and silent Win in Win Win.
Win Win teaches us that lying to make money at the expense of an old man's happiness can lead to family drama, getting disbarred, and a state wrestling championship.
Sex offenders will love this movie featuring pre-pubescent teens wrestling with each other in next to nothing, dime sized boy nipples, and a very obedient young man that wont take much convincing to get into your van.