Not an expert, but it could depend on whether it's considered a dishonorable discharge or not. Common sense would say no, this should be something akin to a medical discharge, but given everything that's going on I wouldn't bet on that.
California could pull this off, given its industry, agriculture, and Pacific seaports. New York, where I live, has lost too much industry and agriculture to be self-sufficient. Joining Canada, though, could help assuage some of those deficits.
He doesn't understand how anything works. You can question his intelligence, and there's the dementia, but most of all, it's his ignorance that stands out.
This guy looks like Fozzie Bear waiting for the audience to react to one of his jokes.