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.
It doesn't matter at all. You are on a mission, and you have chosen to be on exactly one. Use a gold rule, don't be upset if things goes wrong and make a habbit on constaly expect the best - you should be just fine
You can negotiate abit, but not much. Suggest you to check prices in different places first though, to get the best deal. Also be ready that most motorbikes are not insured. As for cars, most of them as well, though you can find the ones with insurance (strongly recommend you that). Safety: always wear a helmet if you use motorbike, always check you mirrors, try not to go when rainy or after heavy rains, NEVER EVER drink and ride, be very carefull in the night time. Also make sure your fuel gauge works fine. Take care!