What is the best visa option for traveling back and forth to Thailand while considering retirement residency?

If you are only leaving Thailand for a couple of weeks while your visa exemption is still valid you can purchase a re-entry permit for 1000 baht at immigration to keep your stamp "alive" so that you come back in with permission to stay until your extension stamp was due to end. That might not be enough time in Thailand for you, but it would likely allow you enough time to do a land border run which will get you another 30 days in Thailand and which can be extended by a further 30 days. This is less likely to cause you problems or questions such as you might encounter flying into either of the Bangkok airports on a visa exempt entry. You are permitted 2 land border crossings per calendar year. You can't be refused re-entry doing a border run this way as immigration staff at the border wont let you leave if you can't get back in. Or if you are wanting more time in Thailand you could travel to the Thai consulate of a neighbouring country (Laos is easiest) and apply for a single entry tourist visa. Most Thai embassies in neighbouring countries (except Savanaket in Laos) require an appointment and will require proof of equivalent to 20,000 baht in a bank account over the previous 3 months. Check the websites of the embassy you plan to visit, for the requirements and any upcoming public holidays and office holidays. Applying for a single entry tourist visa at a neighbouring Embassy is usually a 3 day process (except for Savanaket which is still 2 days) ie lodge your application on the morning of day 1, pick it up on the afternoon of day 3. You mentioned that you planned to visit Singapore, you could consider flying directly into Singapore before Thailand and applying for your single entry tourist visa there giving you 60 days in Thailand when you enter, which can be extended at immigration for an additional 30 days. During that 90 day period you can exit and re-enter Thailand to visit other countries if you also apply for a re-entry permit at immigration in Thailand; 1000 baht for one re-entry or 3800 baht for multiple re-entries within that 90 days of your visa plus extension validity. Unless you are going to exit and re-enter more than 3 times in that 90 day period it is probably best to just buy single re-entry permits as you need them. You can also buy them at the airport just before you leave Thailand but they cost a little more and often the desk is unmanned and you have to find someone to do it for you. Personally I prefer to pop into immigration ahead of travel and purchase a re-entry permit there.

A Multiple Entry tourist visa applied for within your own country still might be the best option for you if you're not feeling ready to bring 800K baht to Thailand. A multiple entry tourist visa can give you 9 months in Thailand if you exit and re-enter just before the expiry date. You could exit and re-enter as many times as you want in that first 6 months of that visa ensured that you will get a stamp for 60 days in Thailand each time you re-enter. The financial requirement proof required for that visa is about of the retirement visa, but does not require that you move a single dollar to Thailand. Neither is there any requirement to purchase Thai health insurance

Winner today of rambling, mullti directional, unsure of plans posting 😁

I am have applied for tourist visa and a marriage visa from the Embassy of Thailand, Washington DC, while being in Mexico and Indonesia. It takes 1-2 weeks (closer to 1 week).

You can start your retirement visa process regardless if you choose to live in Thailand. I would suggest you consider your options. From what I understand there are two types of retirement visas. One you get in Thailand and one you get outside of Thailand and they have different requirements.

You are allowed to enter Thailand 2 times a year without a Visa and will get issued a 30 day exemption each time. Total 60 days ten with no Visa. If over 50 and you don't mind paying 1000 to 1500 usd you can hire local agent who will do all the work for you and get you approved for a 90 day OA visa which they will convert to a 1 year retirement visa. You must be 50 y.o or older. Total is 15 months. After that the agent will charge approximately 500 to 700 usd to renew your retirement visa annually. It will cost you extra if you want to leave Thailand and re-enter during your stay here on a retirement visa.

There’s nothing stopping you applying for the visa online before you get back to the US. You’ll need proof of your address etc from there and the flight details from there to Thailand. It’s all done online so you don’t even need to be there when it’s approved. I understand some Consulates there are quite slow and less than helpful so 2 weeks probably won’t be enough if you wait until you’re home before applying.

I believe 1 requirement is a lease for at least 3 months with your application. Just apply when you decide to reside in Thailand.

Keep in mind there are four different types of retirement visa, all with different criteria