I was on non imm OA for many years but was in Philippines last year when it expired and for past year I have gotten double entry tourist visa's along with my PI fiancee. She is now on a education visa so I want to go back to OA. Will I still be able to apply for a extension or have to start over again?

question 2, my fiancee is now my wife, is she elegible for extension on my OA?

thanks in advance for the help?

You must obtain a non immigrant O visa or convert your tourist visa entry with more than 21 days ramining to a non immigrant entry for 2,000 baht using proof of meeting the retirement 800k in Thai bank account or 65k monthly income or combination. After you obtain a retirement extension of stay (it is not OA) your wife can obtain a non immigrant O visa and extend her stay based on your extension of stay.

The OA visa is what you obtain in your home country - not what you get inside Thailand.