I don't think Dame will get fed up if he believes the organization is doing everything it can (this includes good decision making) to contend with him, but if he starts to think they are not doing everything they can or not making smart decisions, his Loyalty will more than likely decrease to the point he will sign somewhere else to contend. He already has a great NBA and Addidas contract. Does anyone think his next contract will be for money? IT will be to win. IF he sees Portland as not being able to get it doner even if he signs for less? He may well sign for less elsewhere..
IMO, you give 9 years to an organization , you have the right to go wherever you want after that. I didn't even care that LMA wanted to go back to TX. It was his "no, no, don't trade me, I wanna stay---psyche! Never had any intention of staying" that bothered me. Same with the original "Decision". If Dame tells NO "Hey, man, you don't get your stuff together I'm out in 2021" I have no problem with that.
Remember when nobody wanted to go to Cleveland ? I keep hoping Lebron will get finished there and the Blazers can land Kevin Love. That would help Dame to stay ..... I think