It is indeed mandatory with guides and permits in Myanmar. The same with Thailand, although some travellers «slip through» at some of the smaller bordercrossings with Laos, Cambodia and Malaysia. But coming from the Myanmar side theres no way around that. So its going to be costly and boring and very inconveniant as well.
Six months UK-Oz is probably possible but in my opinion (and I have ridden most of that stretch) its not a great way to do it. For example I spent 3,5 months in Indonesia alone and afterwards I wished I spent more time there.
Remember also that the shipping from Dili (East Timor) to Darwin (Oz) takes at least 18-20 days as the ship goes from Dili to Singapore and then returns to Darwin, add up a week of intensive cleaning (your bike needs to be STERIL to get into Australia) and another week of getting the bike through customs, quarantine inspection etc - you will spend more than a month on that alone. I think it would be better if you try to save up more time to spend on your travel.
Just my five cents though...
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In the end everything will be fine. If its not fine its not the end....
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