Yes you can.

@Brad *******

That is correct.

60 day visa exemption + 30 days + 60 day family, then no more.

Sounds like you need to go back and read the conditions of your visa. It is always important to know exactly what visa you have, the conditions, and the requirements for extending it. If you are planning to get the 2nd 5 years, while inside Thailand, you better get organised very soon. But by the sounds of it, you were not anticipating the 2nd 5 year application, so head back home and get another 5 years.

No.

Dean Russell Yes, remotely for a foreign company.

Brads Cat LOL. Tax dodging?? I think you need to check the definition. ;)

Scott Cassio For over 50, and a large passive income, yes.

@Kami *****

So why buy a 5 year visa to stay 179 days a year?

โทมัส ทอม เฟรย์ You can stay in Thailand for 360 days at a time, cross a border and come back, and stay for another 360. You can keep doing this until the end of the visa.