Can I transition from a work visa to freelancing in Thailand with a DTV visa?

Thailand Work Visa to DTV Experience?

I was just curious if anyone has had any experience where they were working in Thailand through a work visa, and wanted to shift to freelancing for foreign clients while still staying in Thailand.

DTV (workation) seems like the way to go in this case but I'm wondering if they're looking for an existing history of freelance already in order to grant DTV in this case.

If my last freelance gig was from 5 years ago, is this still good enough? Or would it be better for me to return home first and get freelance gigs and then try to apply after a more recent history of freelance. Thanks for your opinions everyone :D