The owner of this Facebook group offers a safe entry service.
Fill out their TDAC form, and then on the 2nd page, you would select it as one of the premium options. They will then get in touch with you regarding your entry history to get you an accurate price quote. That's necessary as they have to check with their contacts at the airport before they can give a price.
Not relevant. You need to have your visa printed out, as indicated by the embassy and the e-visa system. You are leaving yourself open to being stamped in wrong if you don't hand your visa over with your passport.
You could very well have a problem. The immigration officer indicated you were spending too much time in Thailand as a tourist. Yet you have now gotten a tourist visa, which is still a tourist entry, and you plan on entering after only being gone for 2 months.
You said you don't want to apply for a retirement visa because of your family, but that makes no sense. You don't have to intend on living in Thailand to get a retirement visa. You just need to meet the embassy requirements. If you get a non-O retirement visa before you go to Thailand, you'll get a 90 day entry stamp and won't have any problems with immigration. You can then open a bank account and put the necessary funds to apply for the 1-year extension, or you can go home and spend a little time and apply for a new non-O before returning to Thailand.
You also have the option of the 1 year non-OA if you don't mind the mandatory insurance requirement.
the OA is a retirement visa so no, you cannot "convert" the OA to permanent residence. You can't convert anything to permanent residence.
One of the requirements is to work in Thailand and pay taxes for multiple years before you can even apply, and then it takes more years after that to process. How would someone on a work restricted visa work and pay taxes?
You making Permanent Residence sound so simple marks you out as knowing nothing about the process. There's a reason very, very few people have it.
You should not get the OA visa if you're planning on getting extensions. Then you have the worst part of both the non-O and the non-OA. The non-OA is only a good option if you don't want to keep 800,000 baht in a Thai bank account, and you're planning on returning to the US at least once every 2 years to apply for a non-OA. But you're going to have to keep the mandatory insurance policy forever.
With a non-O there's no insurance requirement, but you have to keep the 800,000 bank balance in Thailand.
If you extend the non-OA, you have to keep the bank balance AND the mandatory insurance. The worst of both visas.
Yes, but make sure you're aware that Monday and Tuesday are Thai holidays. So you'll need to be fast.
You can pre-fill most of the application on the e-visa website. Then as soon as you enter Laos (I would go Tuesday) upload your entry stamp in your passport and submit your application. Then first thing Wednesday morning (I'm talking EARLY, because they will have been closed for 4 days, there will be a lot of people there), go get in line at the embassy to make the payment for your application. They accept payments from 9-11 AM.