I think that the greater the ability for one to boondock, the less issues they have with finding places to stay. I've rarely traveled with reservations. If I really want to find a place to stay with hookups I just get on the phone and find something.
For longer stays it's out in the woods or desert for me.
Something i recall from a trip my wife and I took to Long Beach, WA.
Stayed in an older RV park along the main highway that was about half full of permanent residents. One of the residents was a woman of in-determinant age who was living in a trailer so old it had flat aluminum sides and a round window in the door.
For some reason every time my wife and I went out to sit in the Sun or have a meal at the picnic table she would push her bicycle up to the empty space next to us and just sit at that picnic table staring at us.
Maybe her television was broken