I think sharp cheddar generally is mature cheddar, not certain if it actually means the same thing though. But a really good stinky mature cheddar should certainly take the roof of your mouth off.
I tend to find mature cheddar shrinks and sweats huge amounts of oil when melted rather than bubbling and going crispy, I think it's 'cause it has so much fat in it. It's not oily when it's not melted though, should be hard and crumbly. Glad to hear you aren't planning to waste a good cheddar by melting it.
Still not convinced by the port, maybe I'll give it a go with a nice strong cheddar sometime. Hope your own cheddar experiment is successful whatever you decide to do with it.
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