You can't do the monthly income method first. The ONLY way to use monthly income for the initial visa or for the first 1-year extension is with income verification from your embassy. And I'm fairly certain the Australian embassy in Thailand does not offer this along with many other embassies. That means your only option is going to be 800,000 baht in a Thai bank account for the first 1-year extension.
To work as a foreigner in Thailand you have to get a job, and a visa that allows work. Foreigners also have a minimum salary they must receive to qualify for a work permit, and that is about 6x more than what a Thai employee would receive, so you have to have some type of special skills that would make you more desirable than a Thai employee because they could hire 6 of them for the same thing they pay you.
Your best option is to find remote work from your home country while living in Thailand with a DTV.
No it would not be processed in DC. It would be processed in Chicago, same as an application through the Los Angeles Consulate would be processed in Los Angeles. And each one has their own rules as well.
Applying for jobs is not working. You cannot work in Thailand on a DTV but since applying for jobs is not working it's allowed. I'm not sure why you would pay for a 5 year DTV if you plan on getting a job though as you will lose your DTV if you get a job in Thailand and get a work visa.
Then you can't have a non-B visa. A non-B visa is for someone who already has a job in Thailand. You need paperwork from your employer to be able to get a non-B visa.