Gilbert would need different local streams of revenue for this to happen. I have heard from people downtown that Gilbert is buying up property. Not sure how accurate it is, but I feel like he sees the long term potential in this city.
First, Gilbert has the casinos + hotel. Its hard to speculate how much revenue this will generate, but that will probably bump up Gilberts wealth.
Second, the Cavs will turn around. Not sure if they will reach their previous value in the short term, but who knows.
Third, I feel like buying up parking space may be a small source of income. Im not talking just the garage adjacent to the Q, I mean all of them within walking distance of the Q. Instead of going into his pockets they can go into the teams. There are a few pro teams who solely own their parking and use it as a great source of revenue.
Next Gilbert will probably develop other forms of entertainment downtown. New bars, restaurants, etc.
Possibly acquire STO, and use that to broadcast the teams he currently owns. However, does anyone know the current contracts those teams have with their respected networks? The cavs in particular?
Once all of this is done, Gilbert might have the ammunition to buy the team, but its not going to happen anytime soon.