Welcome to the HUBB!
I personally wouldn't ship your bikes, If it was a big bike you couldn't do without then possibly but 250s especially if one you haven't purchased yet... no way! a waste of cash and a big headache.
It is definitely NOT impossible to purchase and register a vehicle overseas and that is your best and cheapest option. I travelled SE Asia back packing and rented a small 150cc bike in Lao for 8 bucks a day so that might be a good option for you too. I chose to rent as I only had one month travel but you could easily but a small local bike in Bangkok and travel around, if my memory serves me correctly Vietnam is the difficulty as it difficult to bring in foreign registered bikes. But again easy to buy in Ho chi Minh city and ride up to Hanoi and sell again.
If you like small bikes I would buy a model popular with locals Honda or Yamaha 100cc-150cc scooter type. Most motorcyclist scoff at scooters and wouldn't be seen dead Riding them but they can pretty much go anywhere a bigger bike can as they are super light. I remember struggling up an intense track in my KLR650 and while resting I see a small Chinese 100cc scooter come past 2 up .
The parts cost basically nothing and are everywhere so never a major issue. Just strap on your backpack and away you go
India/Nepal get yourself a Enfield I am planning this for 2020. Not overly reliable but an amazing experience. Otherwise a Bajaj will do you.
Europe you can get bikes pretty cheap and it is fairly easy for foreigners to buy (but not my area of expertise) Just scroll each regional section and you'll find all the info you need...
Hope that sends you in the right direction
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