Heat grill to high. Brush pineapple with oil and grill until golden brown on all sides.
Put pineapple juice in a medium saucepan over high heat. Make a few slits in the habanero with a paring knife and add to the juice along with the cinnamon sticks, star anise, Thai basil and brown sugar. Cook over high heat, stirring occasionally, until thickened and reduced to about 1 cup. Strain and keep warm.
Brush short ribs with oil and season with salt and pepper. Grill on both sides until slightly charred and tender. Plate with pineapple (using 2 quarters of the grilled pineapple) and drizzle with pineapple sauce and red chile oil.
Heat a large saute pan over high heat until almost smoking. Add the chiles and toast for 30 seconds on each side. Remove, let cool slightly and coarsely chop.
Combine chiles, oil and salt in a blender and blend until smooth. Strain into a bowl.