When I'm about to go into a town during a thru-hike, I want to know ahead of time where I'm staying that night. It's not that I feel a need to be structured and have all of my plans set. I never feel that way when planning to camp on the trail. I'm fine with stopping when the time feels right and where the spot seems suitable.
I only want to know where I'm staying when I go into a town. I feel this way because I've stayed in many dumpy motels and hostels on hikes. If I have a choice, I want to stay someplace a little nicer. I guess it's a perk of being older and on a less-limited budget that I can do that.
Of course, I don't often know how I'm getting to a town, but that's different and expected. I can deal with that.