He comes to Thailand with a 30 day visa exempt scheme and applies for a Non Immigrant O visa,
You come to Thailand and use the 30 day Visa exempt scheme, apply for a 30 day Extension of Stay, leave the country and come back using the visa exempt again. If he has the 1 year Extension of STay based on being over 50 years of age (also named retirement visa) you go abroad to find a Thai Embassy to apply for the Non Immigrant O visa based on being a dependent on an alien permitted a long stay in Thailand.
Lots of different procedures and travels, but the hard way seems the way you prefer.
It does not matter where his funds are to apply for the Non Immigrant O visa at a Thai Embassy. But if you prefer to get into Thailand without a visa, get 30 days but only have 15 days to get all things sorted out to apply for the Non Immigrant visa at immigration, it can be done.
He applies for the Non Immigrant O visa based on being over 50 years of age (populair name retirement visa) and you apply fr the non Immigrant O visa as dependent at the Thai Embassy or Consulate in your area.
Husband applies for the Non Immigrant O visa based on being over 50 years of age and 60 days after entering Thailand applies again for the 1 year Extension of Stay.
You as wedded wife, applies for the Non Immigrant O visa based on being dependent on your husband and apply in Thailand for the 1 year Extension of Stay based on being his dependent.
You apply for these visa's before you make your way into Thailand.
The 60 days is assuming based on unable to travel.
If you want to stay long term in Thailand you should get the visa that fits your purpose and length of stay, do not build a long term commitment based on being unable to travel.