It doesn't help that the label mates that left recently had issues with both SM and their new company, like the EXO members and even Taemin ending his contract now.
But it also depends on where he wants to focus next, because he could look for a Thai company that would invest in him. If he has the budget and PR he could build on his existing style. Concept/image wise I think he would be fine because he seems to have a good understanding of himself as an artist now. But the real concern would be the music. Like I trust him to pick good songs but he needs the options. And if his activities are less Korea focused, SM might not be as petty.
Establishing his own company doesn't seem realistic to me unless it's for some other types of activities. Music with SM and other activities handled separately. I wonder what type of deal Winwin has. I doubt SM is not taking something.
Was hoping he would join Running Man Thailand to get some fun content and also good exposure. No more boring survival shows.