In a stand mixer with the whip attachment, whip the cream with 1/4 cup of the sugar and 1 teaspoon of the vanilla extract until soft peak form. Do not whip the cream too stiff; it needs to still be soft when you fold it into the cream cheese. Transfer the whipped cream to a medium bowl and refrigerate.
Switch the stand mixer to the paddle attachment and, in the same bowl, beat the cream cheese, the remaining 1/4 cup sugar and 1 teaspoon vanilla extract, and the 1 tablespoon instant espresso until smooth and well combined. Fold the whipped cream into the cream cheese mixture and set aside.
In a shallow bowl, mix the 2 tablespoons sugar with the bourbon and 1 cup cold espresso until the sugar is dissolved. Dip each ladyfinger on each side into the espresso mixture. Line the entire bottom of an 8-by-8-inch cake pan with an even layer of the ladyfingers. Top with half of the cream mixture, spreading it evenly across the top. Repeat with another layer of the dipped ladyfingers and then the remaining cream mixture. Cover with plastic wrap and chill for 2 to 3 hours or overnight.
When the tiramisu is chilled, spoon an eighth of it into the bottom of a shallow bowl, and top with a scoop of vanilla cream. Top with some hot espresso and serve immediately. Repeat for the remaining servings.