When you rent in for example in Thailand the best place to rent is Chiang Mai (cheapest and many rental agencies) and planning a loop to ride in northern Thailand is very easy and by far the best place to ride a bike is the northern parts of the country. Not much point going south of Lampang/Pitsanulok, just straight roads for many 100s of kms. So doing a loop and return to start is actually the best option if you ask me and there will be absolutely no need to backtrack yourself. The same goes for Laos, rent in Vientiane and do a loop of the northern parts of the country - by far the most interesting bike roads, and come back to Vientiane. And no need for backtracking there either.
In Vietnam they offer reasonably priced services sending a bike back to origin by train either you start in Hanoi or Hochimin.
Buying and selling a bike takes time and energy. I bought a bike in Thailand in 2016 and it took 2,5 months before the registration was in my name. It might be a bit better in different provinces but it will still take time. And it will be impossible to cross any borders in the meantime. And you have 2 months for the whole 5-7 countries...
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In the end everything will be fine. If its not fine its not the end....
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