You are in the Phllippines, want to come back into Thailand with a 60 day Visa Exempt Entry and apply for the 30 day Extension of Stay. During these last 30 days you need to make a short trip outside Thailand and like to apply for a Re-Entry Permit.
Yes, it will be no problem, BUT as you can come back into Thailand using a new 60 day Visa Exempt Entry, I would advice to take the 60 days.
No need for special border runs companies to plan your travels OR a re-entry permit for a short time inside Thailand and than have to leave again.
It would depend IF the person and the employer can meet the requirements, but agree this is Thailand where most foreigners have other ideas than Immigration.
IF you have a VISA based on being over 50 years of age the answer is NOT the first Extension of Stay as this has to be for the same reason why the visa is issued.
IF you have a VISA based on marriage with a Thai Citizen, your wife, than yes and yes there is a financial requirement
NO, you can NOT apply for a new 1 year Non Immigrant O visa,
Sorry to disappoint you and others, but that type of visa is out of stock, you can buy the Single Entry Non Immigrant O visa which gives you once 90 days of stay and than you need to extend inside Thailand with 1 year at Immigration
OR
you might choose for the Multiple Entry Non Immigrant O-A (long stay) visa, but this has more requirements like police check and health insurance.