I could see him try to sell Dish and keep the wireless part to himself.
As far as monetizing the commercial skipping technology, I think Dish would lose a ton of customers if they were forced to watch "targeted" commercials instead of being able to skip them.
I think the current TV model has about 5 good years left. Eventually enough people will drop down to lower tiers or cut the TV cord and do internet only to break the model. Eventually I see fewer commercials and more paid shows. Netflix and Amazon are trying with their own series. Eventually HBO/SHO/MAX/STARZ will join them without a cable subscription. TV channels will then have to decide free of charge with commercials (like the news channels and sports where it is unlikely people will record to skip commercials), or a la carte with no or few commercials.
Why does ESPN have commercials? It is nearly as expensive as a premium channel? They should wise up and act like it and cut commercials down quite a bit, make it feel like a channel worth paying $5-6 (soon to be $9) per month...