Winslow is not allowed on our couch either. He was about the same age when I started to get tough - at night we'd be on the flppr with him cause he wouldn't stop bugging us!
My advice is to keep doing what you're doing. I hate that testing he does! Thankfully it seems to be happening less but I know what you're talking about. But I do the same, tossing him in the crate if he is a repeat offender.
I will say that he never seemed to find his bed to be his own space, and i think that's what made it difficult for us. We gave him our wingback chair, which he is allowed on whenever he likes, and aside from mandatory nighttime snuggles and the occasional couch sneaking it's worked wonders for us.