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Hello to everyone! Sawadee krap! A quick blurb about myself, I am a 26 year old naval vet, I am disabled and receiving my benefits. I also have a girlfriend and her daughter, we have been living in the US our whole lives and a couple years ago, a great friend that I worked with gave me the means to go to Thailand with him and his family who are from Udon Thani. That trip has changed my life and I wish to continue it in Thailand. My family and I wish to move, we are used to a slightly lower quality of living and being there before I have seen first hand how living is and it doesn't bother me. I love the food, talking with other Thais and even the occasional expat. So now here come the questions.
What is the best visa I should apply for for the great length of time I can stay before having to do a visa run. I am pretty well set on either Pattaya or Chiang Mai. Bangkok I fear will be too much big city life for my preference although the school I am interested in does provide an interesting twist. I just dont like traffic and would like to be close to school so I can focus on finishing my degree. Pattaya is more of a laid back place I felt with a great night life and lots of fun things to do, but too far for any school I can use my GI BILL benefits on. Chiang Mai is more laid back, has a school that does provide engineering and is cheaper, but because of my disabilities I fear I may not be able to find as much to do. I would like to live as cheaply as possible but be clean and comfortable. We have a 1yr old toddler with us and want to make sure she has everything she needs to succeed as well as her mommy and daddy work and go to school. So I am looking for others experiences living there and establishing contacts to use when we make the move and have an entire plan set up for getting over there and getting setup for school, a place to live, a babysitter for the little one, and just to make some friends to hang out with and things of that nature, this is all after I recover from my surgeries. Thanks and I greatly appreciate your inputs and help!
 

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I don't up to what extend you're disabled, but by the sounds of it you're pretty mobile.
Since a major part of your plan is education based on GI BILL benefits, I suggest you to contact thr school in Chiang Mai and ask for their possibilities regarding an ED-visa.
I know, I know........ED-visa does recall a lot of negativity, but don't generalise.
If they're a proper educational institute, with proper schedules and curriculums, an ED-visa through them is the best option.

You are talking about "mommy and daddy" are working and going to school, implies that one of you is going to work. That may be another option for your legal stay: The one who is working should obtain a non-immigrant-B(usiness) visa and a WP. At the same time, the not working partner can obtain a so called dependent-visa and rides along on the back of the main-visa-holder.
In this way you don't have to leave the country every 90 days; just report at the nearest immigration is sufficient.

Not sure about a visa for the toddler; maybe the toddler doesn't need a visa.
 
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