Can I frequently travel to the USA while on a retirement visa in Thailand?

Going to close this post for now. If Op has further questions, please contact one of Admins/mods.

Which is more difficult or more "demanding" DOES totally depends on individual preference.

For Mr. A who is traveling between countries, visiting the local immigration office is a bigger task.

For Ms. B who always has insurance for her always and anyway, transferring her funds to Thailand is more painful.

For Mr. C who has an accidental incident record so his only option is Non-O.

These are situations that actually happened to people who are staying in Thailand now.

There is no point to debate which is better for OP by you all who don't know OP's conditions for his decision-making.

Alternative is the Non Immigrant O-A (long stay) visa (retirement visa) which is valid for 1 year and gives you during that year a 1 year of stay on entry in Thailand

After 60 days you can apply for the 1 year Extension of Stay based on being over 50 years of age (retirement visa) and when this 1 year is stamped in your passport you can apply for the mutliple re-entry permit, with that permit you can go and come back using this year until the last date.

No restrictions, just buy a multiple entry permit when you get your extension inked in.

There are multiple visa and an Extension of Stay all called retirement visa, to make things complicated.

With the Non Immigrant O visa based on over 50 years of age (retirement Visa) applied for in your home country gives you 90 days of stay inside Thailand.