In a medium bowl, mix cream cheese and cheddar cheese.  The mixture will be thick - set aside while you cook the jalapenos and bacon.

Heat a grill or flat top to medium heat.  Grill the jalapenos for 5-8 minutes - the goal here is to blister the outside skin of the jalapeno and soften it a little, we want our jalapenos to still have a nice little crunch!   If you have a flat-top, this is where I'd also cook the bacon but cook your bacon wherever you see fit.

Once your jalapenos are cool enough to handle, slice each one in half.  Depending on how spicy you like it, you can seed your jalapenos or leave the seeds in.  Personally, I will remove the seeds from half of the peppers but leave them in the other half.  Roughly chop the peppers into smallish pieces and add to the cream cheese mixture.  Also cut your cooked bacon into bite-size pieces and add to the cream cheese.  I like to put on rubber gloves and mix the jalapenos and bacon into the cream cheese by hand because I feel like I can mix it more evenly this way however a wooden spoon or spatula could also be used.

Regardless of the size of the flour tortillas, we spread the mixture on one half of the tortilla and fold the other half on top so the quesadilla looks like a half circle.  This filling gets deliciously oozy so don't fill your quesadillas too full!   Cook your quesadilla on your flat top, flat grill pan or a skillet.  Cook until both sides are golden brown.   Remove from heat and let cool about 5 minutes to let the filling set just a little bit.  Cut into slices.

Serve with cherry jam and sour cream if desired!

*We've used the large wrap size tortillas and also the small soft taco size tortillas to make these.  Size doesn't matter here but depending on which one you choose does impact how many you need.  For the large wrap size tortillas, we used 4 for reference.