Possibly an METV visa might suit you, 6 months multiple entry validity, with a well timed entry 9 months possible. But realistically a non O with yearly extensions and multiple entry permit, tho you might want to be planning exactly when the extension time occurs by buying the visa at an opportune time to coincide with your travel plans back home.
Yeah bummer about not knowing about the re-entry permit on the final entry stamp, triple check everything in this group in the future before you leave the country on a long term stamp that you want to keep active.
Search the group with keywords of the embassy/consulate city names in the US. My take is it hasn't been difficult for US approval. Just a guess but tax returns would be for digital nomad and freelance route applicants.