This is something I've always wrestled with, even after 10 years of doing big trips.
A lot are happy to just go with the flow on big trips, but if you're someone who likes to have a sense of what they're doing/going then think about fundamentals here and put in place a bit of a structure or system around that, with the caveat of not being too rigid and being willing to drop or change plans in response to circumstances. I think the trick is to have a framework around which plans can adapt and flex to circumstances, as you've suggested.
Couple of thoughts:
- Build some slack into your milage assumptions, unless it's more a liaison route where you just need to get somewhere and you're prepared to stick to it - i.e. if you think you'll be happy riding 300 miles a day, plan for 200 or 250 miles.
- Don't underestimate how roaming adds to your miles - my odometer clocked 40,000 miles for riding from London to Sydney, but whenever I've tried to replicate my route on Google Maps I struggled to break 25,000 miles.....
Hope that helps.
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