Taking into account how other mutiple world champs ie Michael, Seb, Alonso and now Lewis has not been able to add to their WC tally after a dominant run, I would say that it does not favour him atm
The only person on the grid right now that has that kind of negotiating power is Max.
I don't know. If I was in Toto's shoes I would look ahead and try to take Russel, Shumi or whoever and try to build a winning team for the next 10 years. Toto is smitten by the LH marketing effect and probably nostalgia of past accomplishments. It is not good business.