I hope someone can help me, I know my trip seems far away but just want to see what my options are..

Somwhere half way September (2015) I will fly to Thailand (from Amsterdam). At the beginning of October I will fly to Myanmar for a month and fly back to Bangkok on the 28/29 of October.

Now I know I can get 30 days for free when I get back in Thailand and later on extend my stay with another 3,0 but I want to spend newyears in Thailand and will come short at least 3/4 days.. Now I've read that it will be difficult to do a visa run for getting extra 14 days?

Now I wonder, if I apply for 60 days tourist visa before I leave. Can I get a 30 day free 'visa on arrival' because I have proof of leaving the country. Then leave to Myanmar about 9 days later, come back to Thailand and then start the 60 day tourist visa? Or is that not possible to do and those 60 days have to start when you arrive for the first time?

If that is not possible, can somebody please give me my best (and rather cheapest) option on what to do?

Maybe a 2 x 60 days visum and then extend for another 30 days the second time?

If you extend your stay with 30 days. How does that work? You go in and a couple hours later you come out? Or do you have to wait for a day or so for approval? And how strict are they with proof of leaving Thailand with flight? I don't really want to book a flight since I don't have exact dates when I leave or where I will go and rather travel over land? Or should you just book a ticket and cancel it?

For the record:

-half November: arriving in Thailand

-beginning October: fly to Myanmar

-around 28/29: fly back to Thailand

-I would like to stay in Thailand till around half January and then go to Cambodia, Laos etc travelling over land

Thanks!!

A 2 entry tourist visa would be the best choice.

When you apply for the 30 day extension you get it a few minutes after you submit your application and pay the fee.