@Brett ***********
, in that case, you may need to follow these steps.
1. Get you two Single Entry Tourist Visas if possible, or at least for your wife.
2. Once in Thailand open a Thai bank account in your name only and transfer your funds (one bank account is enough). Settle in an address. Get all necessary papers, prepare your Non-O retirement in-country ASAP
3. Apply for it before you still have
*****
days (depends on your address in Thailand) in your stamp. it will be issued and inked into your passport after that
*****
days
4. Once you get your in-country Non-O retirement visa, your wife goes to one of the countries around where she can enter and Thai Embassy there would issue a Non-immigrant visa to Czechs
5. Apply for her single entry Non-O based on trailing family (dependant) to your Non-O retirement there
6. She would come back on Non-O trailing family
7. You will apply for 1-year extension based on retirement when your stamp is remaining less than
*****
days (depends on your address again)
8. Your wife will apply for 1-year extension based on being trailing family to you when her stamp is remaining less than
*****
days
(If you can plan travel appropriately, 7 & 8 can be in the same window, so you can do them at once
As I mentioned about the children, they can do the same way as your wife, or you can decide to let them overstay for a while