Preheat oven to 170°C.
Place halved tomatoes cut-side up on a lined tray and season the pork with salt and pepper.
Roast tomatoes for 90 minutes and roast pork slowly for 3.5 to 4 hours, covering with foil for the final hour.
Cool the pork, discard fat and skin, and shred the meat lightly.
Toast fennel seeds in a pan, then fry onions, garlic, and pork in oil.
Stir in passata and honey, season, and simmer until thick and gravy-like.
Preheat oven to 200°C and brush a 25-30cm square tin with melted butter.
Layer the tin base with 4 buttered filo sheets, allowing overhang on all sides.
Spread half the filling, top with tomatoes and feta, and cover with a buttered square of filo.
Add remaining filling, fold overhanging pastry inward, and seal with a final buttered filo square.
Score the top pastry layers into squares or diagonal lines and bake for 30 minutes until golden.
Dissolve sugar in 200ml boiling water with orange zest and cayenne, reducing for 10-15 minutes into a syrup.
Pour hot syrup over the baklava and rest for a few minutes before slicing.