Thai Consulate in Savannakhet, Laos issues Non Imm O multiple entry based on marriage without finances. The OP can get around 17 months from the visa by applying for a 60 days 'visit family' extention of stay on his last entry.
You only need med clearance and criminal record check for the OA visa, you could go for that visa, it's multiple entry and valid for 1 year, each entry gets you stamped in for 1 year. It does require health insurance.
Your 60 days start the day you enter the country. The visa is valid to use for up to 90 days from the date of issue. You will have problems bording your flight as return/onward travel needs to be within 60 days, the application for a 30 days extention isnt taken into consideration by airlines and Thai Immigration. Your 88 days end flight wont cut it!