Blend cream cheese, sour cream, mayo, Tabasco, and Worcestershire in a food processor. Fold in cheddar and pimentos. Add salt and pepper as needed.
Bring milk and butter to a steady simmer. Whisk in grits and continue to simmer, stirring frequently. Cook for about 20 minutes, or until grits are tender and creamy. Add salt and pepper as needed.
Fold in about one cup of the pimento cheese and hold warm.
Heat oven to 400 degrees. Arrange bacon on a sheet pan lined with parchment or with a Silpat nonstick pan liner. Bake for about 20 minutes or until desired crispness is achieved. Remove from pan and drain on paper towels. Rough chop and reserve for garnish.
Puree vinegar, honey, bbq sauce, pepper flakes, garlic, tomato paste and oyster liquor(if using) in a blender or food processor until smooth. Continue processing while slowly drizzling in canola oil. Adjust seasoning with salt, pepper and Tabasco.
Lightly dredge oysters in cornmeal seasoned with salt, pepper and cayenne. Deep fry at 375 degrees for about 1 minute. Drain on paper towels.
Fill a small bowl with pimento cheese grits, then oysters. Drizzle some of the vinaigrette over the top and then add crumbled cooked bacon and chives.
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