Finally! An answer to my question: WHO DO I HAVE TO MAKE FRIENDS WITH AROUND HERE TO GET A MEDIUM RARE BURGER!?
Turns out, it's the fine people at Bestellen. We are definitely friends now.
We went at 6pm to avoid the crowd and start things off right with buck-a-shuck oysters (every night from 6-7!!). They were nothing fancy, served simply with fresh horseradish and hot sauce. I'm a firm believer, however, that if the oysters are good quality, that's all you need. And they certainly were.
We enjoyed them with a white wine they had on special during the same timeframe. I don't remember what it was called but it was $5/glass and it married perfectly with the brininess of the oysters.
Once we finished our "surf," we moved on to "turf" and split the burger and fries.
The meat is ground fresh everyday so we felt good about ordering it cooked to the recommended medium rare. It was juicy, rich, and delicious. Fries were good too and so was their house made ketchup!
We'll be back for sure!