Do you plan each day of your trip or do you wing it? I am going on a 4,400
mile trip and have it half planned. How far a head do you plan?
I do the same as Russ, I set down and plan where I want to be at the end of the day but let fate dictate the journey between. If I'm in an area of great interest I may even add a day or two. When I'm on a trip that involves reserving a site for say a week or two I will usually haul arse out there and then do excursions from that area Base camping if you will. I do that a lot when I visit family.
Jack, excellent question and there are sooooooooooo many variables plus personal preferences its hard to give a general one size fits all answer in my opinion. For example, a few years back I took a 6000 mile trip to eight national parks over like 42 days AND I HAD RESERVATIONS EACH AND EVERY NIGHT. The main reason was its hard to get in some of the popular National Parks unless you have reservations. On the other hand, I've taken trips where I wing it as far as where to go and stay and that was also fun. The thing is I like to know approximately where I'm going and have a place to stay because if you're way out west there may not be any Walmarts or Truck Stops just in case you're not near any BLM or Natl Forest land or potential boondocking spots. So, Id say if your destination is a popular National Park you best plan and reserve a site for those nights, but while in transit where there's less people and demand its not as necessary.
The other part of the equation involves just how much boondocking capacity you carry. If you ONLY have enough water and solar and electrical energy storage for a night or two your ability to wing it is less flexible, but if you have enough food water solar and energy storage to last at least a week or more as I do, you have much more flexibility.
There's a fun time and place for winging it, but there are times when you better have a plan lol
Of course, this is strictly a persons choice and to each their own, no right or wrong answers here !!