1. A smallish bike, 250-500 cc. Absolutely no need for a huge behemoth exspensive bike. A Honda Crf250/300 will never be wrong in these countries as its assembled in Thailand.

2. Ship Darwin to Dili (East Timor) If you ship to Malaysia you will have 2-3 days of riding, 1 day to ride through Malaysia and 1-2 days to ride through Thailand. Myanmar is closed for overlanding and will most probably be for a good while ahead. So its not possible to ride through Myanmar. You will have to ship to India. Actually its better to ship from Malaysia to India/Nepal than from Thailand to India/Nepal. So that means that if you send your bike to Malaysia you might as well send it directly to India….
Ship it to East Timor and you will at least have 30 days of riding in Indonesia + 2-3 days in Malaysia and Thailand.

3. Roby @Superbiker in Surakarta City, Java island - Indonesia. Sunny Cycles in Kuala Lumpur, Riders Corner - Chiang Mai northern Thailand (guesthouse, restaurant, rentals and Rideasia forum)

4. Plenty of cheap accomodation all the way through East Timor, Indonesia, Malaysia and Thailand. Just be sure it has safe parking for your bike.

5. See point 3. Also if you ride a Honda - get spares at a local Honda dealer, if you ride a Suzuki - the same and so on.

6. If you ship directly to Malaysia it will be approx 3 days of riding, 1 day through Malaysia and 1-2 days through Thailand. If you ship to Dili - then add another 30 days.

7. I dont know your habits but it should be possible to live for approx 50 Aussie dollars a day, shipping and insurances not included.

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In the end everything will be fine. If its not fine its not the end....