I understand where you are coming from. I used to board at a place where I could go ride on some gorgeous land and I would just go ride there and take off Hunny's bridle and then let her graze while I sat and listened. Where she is now is a better place for her to be and she is happier, even though the riding area is flat farmland :( However if we want to trailer somewhere to ride it is an easy and quick trailer ride (only about 30 mins to river bottoms or hills each way)
I read the thread and it does sound like the move will be good but will take some time getting used to. The new barn sounds like the BO has a good head on her shoulders and is working within the means of the barn. It may not be enjoyable at first, but once you get used to the people and the facilities I bet you will fall in love with the place for different reasons.