Admittedly I just let my partner plan the bike routes for our loaded trips. His style of planning has been and continues to be..book first 1-2 nights somewhere, then leave it loose in between when he is unfamiliar with the area (ie. unpredictable hills, lousy weather, etc.) and book last 1-2 nights. Middle of trip, we might try to book a place 1 night in advance if I know I can do the distance after a few days of consecutive loaded cycling.

Looking back, it worked out ok especially when we would roll into a strange town, I would choose the local b 'n b or hotel without much prior research. He left the non-camping accommodations to me to choose. We've had some great surprisingly nice accommodations --on the fly..

I like to have a general idea of where we are going in advance for a multi-day/multi-wk. bike trip. But I prefer not to get overly detailed in knowledge in advance, about the road grades or whatever difficulties lie ahead. I seem to do better, not knowing TOO MUCH to freak me out.