One challenge for me is tour fitness.
I might be cycling quite regularly in the months prior to the tour, but invariably, it seems, in the month or six weeks just before a tour my exercise level slackens right off. I'm usually busy doing last minute preparations, and in the case of my two longest tours, those last minute preparations included packing everything up and putting everything into storage. So there was essentially no cycling going on.
And then I start the tour and discover that my fitness level has dropped right off. So I think I should be able to plunge into it with an 80 or 100 km day ... but that is just not happening.