Haha funny how we have similar names and are both in the Chicago area. Something in the water, I guess.
Id keep the apple care. You already paid for it so obviously you can afford it, and you no longer have to worry about it for 2 years. You also won't miss the $100 that went into it already.
A $50 deductible and same day replacement at an Apple store up to 2 years from now if you drop it or something goes wrong will be a lot easier to swallow than $550-$800 (or more depending on your model) or hours and days spent on ordering replacement parts, waiting for shipping, reading DIY guides, etc.
Even if you don't use it for 2 years at least you won't be panicked about taking your iPad on vacations, to coffee shops, etc. where you may have an accident cause you'll know a replacement is just $50 away should something bad happen.
That frees your mind up and lets you enjoy it the way it was meant and not keep it locked up in your room because you're afraid it will break.