I tried them again last night, this time cooking the brownies completely and then, right when they came out of the oven, shoving the rolos into them. That way the rolos melted enough, but didn't take over the consistency. And they look and taste GOOD. I barely made it down to the main office (which is literally downstairs) just now with any left on the plate, they were snagged by hungry, angry-over-MCAS teachers on the way.
Below are pictures of the process, the mess and the success.
Ingredients ready to go (I'm not sure why I decided the oil needed to be shown...)
Brownie batter in mini cups ready to be baked
After being removed from the oven the first time and having the rolos stuck in.
What it looked like after I gave up on getting them out in cup form and shoved them into a pan
Then scooped into a bowl with ice cream and a rolo
Finally, the remake. This time the brownies were completely cooked first and then the rolos were put in.