Put a medium pot over medium-high heat, add a drizzle of EVOO and the bacon and cook until the bacon is crisp, about 5 minutes. Remove the bacon with a slotted spoon and drain on paper towels.
Pour off a little of the bacon fat, leaving a thin, even layer. Add the potatoes, onion, celery, bell pepper and bay leaf to the pot, season with salt and pepper and cook for 7 to 8 minutes, stirring occasionally, until softened. Stir in the flour and cook for 2 minutes. Add the chicken broth and, using a wooden spoon, scrape up all the brown bits from the bottom of the pot. Add the milk, cover the pot and bring to a simmer.
Run your fingers through the crabmeat to check for shell bits, then combine with the thyme and seafood seasoning. Uncover the pot, stir in the crabmeat and simmer for 6 to 7 minutes, until the potatoes are just fork-tender and the soup has thickened. Finish the chowder with the Sherry and serve with the crispy bacon, chives, oyster crackers and hot sauce.