To expand slightly, what's the point of seeing how fast you can complete an exploratory experience, a journey of discovery, a search for the heart of a country and the heart of a rider?
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"Milke Markers" on trails or roads are unlikely to be very accurate, just a guide. The roll out method is by far the most accurate as the nominal tire size given by manufacturers is often not exact either. I have a set of 700-32 marked tires that measure an actual 26 mm installed on standard road rims and their roll out confirms the actuual measurement. A GPS can give very accurate distance measurements and can be used to calibrate a cyclometer if you have access to one.
Also, i plan on having my parents mail things to me along the way, including valuables like money or whatever else. How exactly would I go about it. Would I simply have to know where I will be in, say, a week, tell them the city and have them mail it to the post office? How does that work to have them mail things to me along the way?
I would not have things mailed to you. Trying to figure out where to have things mailed and then hooking up with them is a major hassle. You will either get to the town too early and have to wait, or you will get there too late and the mail has been returned to a regional office, or the post office is closed, or you are at the wrong post office. I had to have some special order tires mailed to me, and I will never do that again. You do not want to have any appointments when living on the road; you want to be able to live life foot loose and fancy free, and go where the wind blows you. Mechanicals, side trips, detours, and hooking up with other riders are all possibilities that you don't want to have to forego because you have to be at a certain town at a certain time.