Yes, many people did it this way in the past. Are you asking if it's a good idea to do it now? It might be better if you ask if they managed to do it in the past 6 months as the banking situation changed this year, making it virtually impossible without an existing bank account or using an agent.
if you've got the bank account etc already, you can enter Thailand visa exempt and apply for the non-O again inside Thailand, but I'm not sure that makes it any easier. Good luck.
If you have a 1 year extension and purchased a re-entry permit, as long as you come back to Thailand a couple of weeks before your extension ends you should be fine (allowing yourself enough time to apply for the next extension).
As Brandon said it's unclear if you have a visa currently, did you get a re-entry permit before you left Thailand? If not you are starting again. Do you have a bank account in Thailand? The simplest and easiest route for people to retire here is: 1. Apply for 90 day non-O retirement visa online before coming to Thailand. 2. When you get to Thailand open a bank account in the first week. 3. Deposit 800,000 baht into the account. 4.Get a list of requirements from immigration to extend your stay and wait 2 months. 5. Return to immigration with all the documents on the list and apply to extend your stay. Good luck.
The easiest route is: 1. Apply for a non-O visa based on retirement for 90 days from the Thai Embassy in your country. 2. Enter Thailand ensuring immigration stamp you in with the visa. 3. Go to immigration and get a list of requirements to extend your stay and a residence permit. 4. Open a Thai bank account. 5. Deposit 800,000 baht in the account within the first three weeks of arrival. 6. Wait two months until your money has been in the account for two months and return to immigration with all the documents on their list. Fill out one a4 form (easy), a map of where you live (copied from Google), some passport photos, lots of photocopies, pay 1,900 baht and you are good for another year.
Ignore Bill's advice or you will regret it when you get here. It used to be possible a year or two ago to come without a visa, but now you will have massive problems. Listen to the advice given by the moderators (Brandon) and people like Lynette.