Ryan, that is a beautiful looking cheese, but sadly not how the Stilton's in the video look.
It almost looks like a Camembert skin with soft inside, for a Stilton that means there is definitely something wrong under that skin.
In order for it to deform in shape like that it must be high moisture content, when I look back at your curds and picture of your cheese after it's initial turn, it looks much moister than the milled curds in the video.
Also, I think the rind after 2 weeks should have hardened up by now, you could try reducing the humidity, but frankly it looks a little late.
How about cutting it open down the middle twice in two parallel lines, like in the video where they cut Stilton with a wire, and eating the slice, might give some clues. You could then sandwich it back together, but sadly I don't think this one is going to make it all the way.
Not trying to be negative, just my 2 cents and ideas . . . John.