By all accounts it is very difficult but has been done. However I'm not sure if anybody has been able to drive their vehicle all the way through Myanmar. A couple of accounts suggested that the officials insisted on driving the vehicle from the Indian Border through part of the country whilst the owner had to fly from India into the centre of Myanmar. They were then allowed to drive the vehicle from the centre of the country out to Thailand. I also remember reading something in the account that the vehicle didn't turn up for 10 days with no explaination of where it was and then appeared again.
You should be able to ship fairly easily from India to Singapore although it probably means putting the vehicle in a container as apposed to being able to put on a car ferry.
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