I'm flying to Tirana, Albania, on Tuesday. I don't have a room reservation yet. In fact, my first reservation is for the night of August 22, when I'm meeting a friend in Milan. The last time I checked booking.com, early May in Tirana didn't look like a problem. I hope I don't get an unpleasant surprise when I get around to booking a room in the next few days. It's a good thing I didn't pre-book Albania, North Macedonia, Montenegro and Serbia like most folks would, because about a week ago I decided I wouldn't be ready to get on a plane on April 30 as originally scheduled, so I delayed my departure by a week. And I had no reservations to unravel! It was wonderful.
This does not mean I'm not a planner. I plan my sightseeing options very, very intensively. I'm low-maintenance where hotels are concerned, though price-sensitive, so hotel bookings are made farther ahead or less far ahead based on availability and price level. Rural Scotland (availability), Norway (cost), Italian lakes and Dolomites in season (both) are examples of places where I pin down hotel rooms many months ahead of time. Estonia, Latvia, Lithuania, Poland (not Krakow or Gdansk) and this year's Balkan countries are examples of places where I'm willing to risk a bit of rate inflation in order to retain flexibility.
I find it very difficult to anticipate how many days I'll want to stay in cities of any significant size on a first visit, and I do not like being forced to move on with things unseen and undone. It gets a great deal easier when you're revisiting a place you've been before.