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.
For me, Thailand wins hands down for infrastructure/Food (except Korean, PI wins there) But (again IMHO) the beaches/sea are better in the Philippines so it's close, but on balance as a place to live day-2-day, I'd have to choose Thailand. For a lot of non-Expats (by that I mean people not moving there for their job/career) it often comes down to their "Partners" which adds an individual dimension that is impossible for anybody else to comment on, but I'd strongly suggest that, this aside, if you can afford to live in a good place, you'd pick Thailand over the Philippines (& I love PI, Mindanao, Davao City, especially). Obviously Visas are a lot easier in Philippines than Thailand, so by "Can Afford", I'm assuming that the relevant visa would be comfortably covered, if you can't afford to live in Thailand because of the Visa costs then the Philippines or Cambodia might be a better choice.