It depends if you fit their profiling and stereotyping, in which case it can be just once, as they determined you are trying to stay here long term as a tourist, and they do not like those people at all. If you have dreadlocks and a backpack, then expect a rejection the second time. Regular tourists don't get the 30 day extension.
as it stands now you will not meet the requirements for the DTV to work remotely in Thailand. You don't seem to have any documentation whatsoever to prove you have a legitimate business. At the very least do you have a business license?