Consider your budget, know the locations of Thai Embassies and Consulates, check transit options and hotel prices...go where you might see something different with the required documents and try to travel back in at a land border.
Also, make sure the embassy or consulate is open on the dates you want to go and if an appointment must be made prior for a specific date.
The whole thrust of current enforcement on using exempt entry or tourist visas to stay long term, seems to be the desire to get those that can stay long term onto getting those visas that allow them to, and limiting those that don’t want to or can’t qualify for longer stays.