Have a look at Julian & Ali Travels.
Julian and Ali had already driven from Oz to Europe so had a lot of experience with visas, but of course the return trip was on a different route so they had to start again.
Not suggesting most people would go to this detail with their planning but Julian thrives on it - but just setting off and hoping for the best is likely to be very problematic too.
That was the planning part and despite the detail, the execution was far from smooth at times. For instance in Turkey they had to make several major detours to arrange visas for the next couple of countries and there were times when passports had to be couriered back home and return which is not what most of us would want to do with our passports full of hard-won visas.
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