it is not that easy for everyone. We don't have to label someone stupid if they find it challenging to manoeuvre the paperwork and all requirements. It can be nice there is the choice of using an agent if you want to.
the information Brandon, Chris and John have given you is correct. You can do a border bounce without getting a re entry permit. Then you enter Thailand receiving a visa exempt stamp on arrival which gives you 30 days. This you can extend with another 30 days at an immigration bureau in the country. An agent can do it for you if you don't want to travel to the immigration office.
Within this time you'll need to get all your paperwork sorted as you'll have to apply for a non-o 90 days with still at least 15 days left. After those 90 days you can apply for the one year retirement visa.
Using an agent is highly recommended, immigration often does not like having to put too much time into getting you to understand what papers the Thai government requires as it's a lot. If you have any specific questions or need more recommendations feel free to message me. My husband works closely with immigration and can offer you complete clarity on the whole process.
I am Dutch and made the move to Krabi over twenty years ago. I am married to a Thai and living on Koh Lanta, Krabi province. We have an 8 year old daughter. I'd love to help you, answer any questions you might have concerning your move here.
In most cases you can show a reservation of a return ticket or book something you can cancel just in case they ask about it. You can travel to Thailand without applying for any visa beforehand. There are great language schools and Muay Thai gyms that can provide the paperwork for an Education visa. The benefit of choosing the language school is that you can learn online from wherever you are in Thailand. When it comes to Muay Thai you'd have to go to the gym to follow the classes.
Feel free to message me sharing your vision of what you guys are looking for then I can give you all the details that would be useful for you, timelines, process, prices etc.
Wishing you guys good luck and hopefully lots of fun prepping for this new adventure for your family.