I have a hard time drawing a conclusion based on Gisele’s desires because it appears as though Tom is still in charge of his decisions, but if/when Tom begins to sit on the fence about it and is openly crafting his docuseries to end on a note like that, I think Gisele’s desires could factor more into the decision than they previously had.
If Brady is feeling unhappy and under appreciated, he would be more likely to give in to Gisele’s nagging. As far as the money goes, there’s plenty of money for an extension. Actually, it could even lower his current cap hit and free up more money. The same goes with Gronk.