Is it feasible to transition from a tourist visa to a work visa or spousal visa while living in Thailand?

Our Visa Plans

Given the tightened immigration and work-permit enforcement in Thailand, we’d appreciate some real-world advice on whether our plan is feasible.

I will be entering Thailand on the Destination Thailand Visa (DTV) as a remote freelancer (foreign clients only). My wife will initially enter on a tourist visa for her to look for a part time teaching role, while she studies online for her teaching qualification. If she decides to teach locally, the plan would be for a school to sponsor her work permit. If she does not work and only studies, we would look to transfer her onto a spousal/dependent visa under my DTV.

Does this approach (tourist → either work visa or spousal/dependent) work in practice under current enforcement, or are we likely to run into problems with conversions, overstays, or visa runs?

We want to do this cleanly and legally from the start — any recent experiences would be very helpful. Thank you