Do you have any friends in the US that can handle it for you?
I use a mail service and claim I live in the US. The mail service will open the letter for you and send you photos. That may not be too much help but if you tell SS that you live with a friend, and that friend process the paperwork for you, you could buy them a steak dinner and save money on postage.
Any advice for using the income method? I have been sending 65K from a foreign bank account for over a year. I think I will be using the Pattaya immigration office.
I pay 2000-2500 baht for a taxi from the airport to Pattaya.
It's pretty simple. You get off the plane, go through immigration, collect your bags, go to the taxi stand, get a taxi. The taxi driver will not likely understand exactly where you want to go so you may want to have a print out of your reservation that has the address and phone number. It's likely the driver will call the hotel to figure out where to drop you.
It's not a bad idea to download Grab, to get a quote of what a fair price is, then show that to the taxi driver.
AIS is probably the better phone service provider. You can get a SIM card after you collect your bags. It's probably a good idea to have your phone/internet working before you get the taxi.
Pattaya is expat friendly. You can get whatever you need once you arrive at your hotel.
If she is super hot and in to you... She was probably not born a women.
You could live in a temple and eat rice for next to nothing.
If you want enjoy $100 steaks at a 5 star hotel everything, that will be a bit more costly.
I rent a place near the sea, in pattaya, $500 month. I eat in mostly and travel every few months, in total I transfer 65,000 monthly, and a little more every so often.
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This is a pretty good site to get an idea of how much things rent in different places. You'll have to do a little more surfing to determine how much tourist stuff costs.
SCUBA instructor or English teacher are the two most popular jobs for expats. The SCUBA instructor would be cool if your GF is somewhere near tourist ocean side town. From what I understand it's difficult to get hired as an English teacher after 50 (I taught for a couple years previously).
Now you're left with...
If I were you I would focus on acquiring remote work skill-set.