In a medium bowl, combine strawberries and 2 tablespoons granulated sugar. Let sit for 15 minutes.
In a wide, shallow dish, whisk together milk, eggs and remaining granulated sugar.
In a small bowl combine softened cream cheese, chopped chocolate, confectioners' sugar and vanilla. Spread cream cheese mixture over one side of 6 slices of challah bread. Top with remaining plain challah bread slices. Dip sandwiches, one at a time, in egg mixture.
On a flat griddle pan or in a large skillet, over medium heat, melt butter. Add French toast sandwiches, a couple at a time and cook until lightly browned, 4 - 5 minutes, and until cream cheese mixture starts to ooze just a bit.
Serve sugared strawberries and a dusting of confectioners' sugar over each French toast sandwich.
Notes
The original recipe used semisweet chocolate. I used milk chocolate because we prefer it.
This recipe reprinted with permission. Find the original recipe in Florida Strawberries - A Taste of Summer All Winter Long