I think he may feel trapped because the majority of people who attend his shows are casual fans that want to relive tracks that they danced to in high school or when thery were young and then they invite other casual fans who decide it's an 80's night out with Prince and if they hear stuff from the 90's or the 00's they're like WTF is this shite, and then he gets bad reviews in the local newspapers, whereas if he keeps them happy but pisses off the org, only the org gets their knickers in a twist. If he specifically had a tour titled the "Art Official Age Tour" or the "PlectrumElectrum" tour people would immediately know to expect to hear songs from those albums and hopefuly more of the non-fan casual fans would stay home if thats not what they're there to hear.

And I've heard of SOS band but I have zero clue what they play and doubt I'd spend money to hear anyone play covers of them. Generally when that type of thing works (e.g. when Meshel Ndegeocello did the Prince tour) it works when the person or group you're covering is 5x more popular than you are. If Prince did a show of Madonna, Beatles or MJ songs that might work.