Ok...
I watched the video on YouTube.
My thoughts right away are:
1) Fresh pineapple has enzymes that break down protein quickly. Pineapple capsule (with moderate heat) + meat filling = high potential for "mushy" meat.
2) It basically steams/braises inside the pineapple at a temperature that the enzymes do their most work. I'm not sure about you, but that doesn't seem appealing to me at all.
The enzymes work slowly in cold temperatures and are deactivated when exposed to high heat (e.g., canned pineapple).
What would I do differently next time?
Personally, I would make something like Al Pastor on the rotisserie, if you were going to combine pork and pineapple. However, one idea if you really wanted to make it again would be to prep the pineapple capsule like you normally would. However, instead of stuffing it straight away, throw it on the smoker first and cook it (both halves open/exposed). Pull the capsule off and then put the meat in. Continue cooking. Or, you could take a hand torch and sear the inside of the pineapple. Then fill it?
You could also do that and start the meat on the smoker. Halfway through, combine them together (or combine at the end during a rest).
Just some thoughts...YMMV.