FYI. I don't know how the legal system works in different countries but you may want to look into setting up a trust versus a will in case of death. In the U.S., a trust allows you to bypass probate court and therefore avoid some costs and taxes. I would consult an attorney or do some research online. A trust is a little costlier to set up but may be a savings in the long run.
You can renew your visa exempt stamp (in 60 day chunks) for 16 months Tiz & technically possible for another 8 months after that with clearance from the PI Chief of Immigration office, but there's also the option of the 5/20 year Thailand Elite card (again we're talking about being able to afford to live in either country comfortably) which is even easier (at a price). If I was staying long term in PI, I'd go down the SRRV route, $20,000 US (aged 35-50, $10,000 if you're over 50) buys you the right to live, work, own a business there & unlike the TE the money is still yours should you choose to leave the Philippines. How are you finding Manila? Missing Singapore yet? I moved to KL 4 weeks ago & not missing the place at all, I was due to go back towards the end of April for my mates ROM, but am in Thailand for Songkran the week before so have decided to stay there for a couple of extra weeks & catch him at his real wedding in Bali at the end of May.
I was reading today about long term stay in Philippines. If you qualify for a retirement visa, then either country is easy to stay in from a visa point of view. But if you are under retirement age, or your partner is under retirement age and is a foreign national, then long stay tourist visa can be obtained for the Philippines which only requires leaving the country once per year. I don't know what options would be available in Thailand.