Can I apply for a tourist visa in Thailand multiple times a year to stay long-term while freelancing?

Are you willing to personally guarantee that? Each country has a different treaty and what is covered under it...

@Cissi ********

I'm not sure about that. Both visa classes state "employment prohibited" on them, meaning no employment in Thailand. You can, certainly in practice anyway, work remotely on ANY visa or visa exemption.

Not sure where you're getting the idea you absolutely need a DTV to work remotely here. Ideally, you should, particularly if your intention is to spend an extended time in the country or even (sort of) live here.

If the authorities were actually hunting down those working remotely and fining the ones on tourist visas or exemptions (despite the fact the DTV has the same conditions on the visa), no one would dare come here as a tourist and send an email and this would greatly affect Thailand's reputation.

In short: the authorities don't care about remote workers unless they're taking away local jobs or people are doing something illegal or immoral, even if it doesn't involve Thailand directly (such as selling sexual services, selling weapons or running an online casino). They've essentially said: we are OK with remote workers / digital nomads. If you come for a short time, no need to do anything. If you come for an extended period, please get a DTV.

@Wannikea ********

Ditto.

@Kevin *******

Fully agree. Great comment.

@Gerry *******

Yes, Spanish Tax is crazy high.

@John ********

@John ********

Great advice.

@Roberto ********

checkout these guys: I don’t pay tax anywhere and it’s legal.