Special equipment: 8 (3 to 4 1/2-ounce) ramekins; a cookie or biscuit cutter, the same diameter as your ramekins
Cut the crusts off the loaf of bread and slice into 1/2-inch thick slices. Use a cookie cutter to cut out rounds of bread that will fit snugly into your ramekins. (You can make additional rounds by cutting 1/2-moons around the edges of a slice of bread, then assembling them into whole rounds later.) Place the bread rounds in a baking dish or a sheet pan with sides. Cut any scraps into small cubes and reserve for another dish.
In a saucepan, heat the half-and-half, cream, salt, and vanilla bean over medium heat, stirring occasionally to make sure the mixture doesn't burn or stick to the bottom of the pan. When the cream mixture reaches a fast simmer (do not let it boil), turn off the heat. Set aside to infuse for 10 minutes.
In a large mixing bowl, whisk the eggs and sugar together. Whisking constantly, gradually add the hot cream mixture. Strain into a large bowl to smooth the mixture and remove the vanilla bean. Pour over the bread rounds and let them soak for 15 minutes, gently turning the bread over once.
Fill each ramekin with 1 soaked bread round. Spoon a tablespoon of jam into each ramekin, add some chocolate chips, if desired, then top off with a second bread round. If there is any remaining custard, pour it over the ramekins to top them off until they are almost full. Let soak in the refrigerator another 30 minutes.
Heat the oven to 350 degrees F.
Arrange the ramekins in a hot water bath. Bake until just set and very light golden brown on top, about 25 to 30 minutes. Dust with confectioners' sugar and return to the oven for 10 more minutes to caramelize slightly. Serve warm or chilled.