Anyone care to chat about what am expecting to find?

I have so many questions, that Id love to just find someone I can chat with 1 on 1, via facebook, email maybe even here..... so my story,
I was living in Mx City for a few years, mostly funded by my online job (300-600USD a month) and it was enough to get me by, I had saved money for years to open a bar, live venue place. But that did not work out (yes Mexico is as corrupt and horrible as you would expect) but I had to try....well as of a week ago am back in the States...and I HATE IT, I knew a long long time ago I did not want to live here, and more so then ever now I have had a taste of life in another country.

So I will never go back to Mexico, next I want to try SE Asia,
Thailand looks great, and friendly for tourists. Am thinking Chiang mai, as per suggestion from an online friend. Says you can get that big city feeling and not spend as much. 
Part of my online job is working with "models" and Id love to continue that work while am there (no its nothing nude or erotic) . am also in the process of getting my TEFL (160 hour course) online, and looking to teach English maybe part time.  (both as its very interesting and to help with my visa)

Speaking of Visas, I'll most likely go for a non-tourist re-entry visa? I think its called (1 year and having to leave every 90 days) from what I understand that can be easily changed into a work/marriage visa?

At this point am going to ramble, Id love to pick someone's brain on this topic if you have time!

I am pretty sure you not going to get a work permit for the online model work.

Teacher sure, But you be fighting with a lot of others for a low pay job.
Only a few Teacher with the right degrades get the high pay job.
Special in a town like Chiang mai with so many foreigner going that way.

Tourist Visa is Single Entry 60 days, That you can Extend at Immigration for 30 days.
Or Tourist Visa Multi Entry, That give 60 days per entry, That can be extend at Immigration for 30 days per Entry. Valid for 6 Month, If Smart can give you nearly total of 9 month in Thailand.

You Can NOT work in Thailand on them (Legal).
If you find a good employer(School) that have the paper work is correct, Going to get he correct Visa is "easy", Same for work permit with the correct paper work.
Sadly many employer dont have control over their paper work, And this can then be a problem.

If you never being to Thailand before, I think it is a good idea to come for 60-90 days and see & feel the country & people for yourself, Try Chiang mai, You might (or not) like it, Thailand is not for everyone.

If you a younger person that dont have you old age pension plan under control, Then think over it before moving here, It is not going to be that easy to save up on a little Teacher salary, Even harder if/when you find person to share you live with.
And can be hard to start a familie and after X-XX years have to move to make more money for old age pension..

And Thai Immigration are tighten up on people staying in Thailand with "wrong Visa"
Please remember a Tourist Visa is not to stay and live full time in Thailand, It is to be a Tourist.

Id do hope the best for you, And that you find what your looking for.

Kindly.

If you are looking for a job in SE Asia then at least get your TEFL certificate first. Some countries like Indonesia officially require 5 years teaching experience too, but I think many people do not have that experience. Also, look at China and Taiwan and perhaps Japan too. All these places are interesting to live and work.