I have seen some people talk about some of the outlying cities in the Philippines as a consideration. I have not been there, but two people on the internet that have posted extensively about retiring to the Philippines and are retired there are as follows:
Life Beyond The Sea
https://www.youtube.com/user/enricosuave263/featured
He posts an extensive library about his experience of retiring to the Philippines and in the videos talks about everything one could want to know about moving, living there and what you would be dealing with on a day to day basis. He is also available for private consultation if one wishes to pay for his time and ask questions of. (It sounds like you would benefit greatly to be able to ask specific questions about your situation and medical needs.) The last I recall from the videos I have seen is he is living in Dumaguete and seems very happy. He also posted a video about the different standards of living available to one depending on their monthly income.
Exciting Cebu
http://www.excitingcebu.com/
This guy writes about his experiences in Cebu City and retiring on a disability income from a government job. While the income is 'ok', it is not great as he seems to not have much left over each month. (From what I can tell, it sounds like his monthly income is around $1,000 USD per month.) It is possible that his monthly income might be somewhat near your own. At this point he has been there something like 7 or 8 years so far. He has a number of postings on getting medications in the Philippines and generic alternatives since some brand names are not available plus talks about arranging banking and deposits of his disability income from the US to a local bank. He has a girlfriend that helps him with a lot of navigating the bureaucracy of various organizations and how they dealt with them. He also sells what he calls an "Exapt Training" manual where he goes over the options for arranging things and how things work there plus has another book just about transferring money from the USA. I did purchase a copy and, while I have not had the chance to travel there, do believe the information is useful.
Both men talk about dating in the Philippines and what to expect when dealing with people on a daily basis and the cultural differences. Both talk about getting and maintaining a visa to be able to stay in country on retirement.
If I had to sum up to expect and prepare for, I would summarize it as follows:
1: Remember that you are in another country. One of the big things is to not make a local 'lose face' or be too critical of the government. There was one video posted by another in country person of someone being deported for throwing a screaming fit at a local policeman. (In the USA it is 'usually not a good idea' and could get you a ticket or worse, in the Philippines it can escalate to one being deported and not allowed back in for a few years.)
2: Most locals will not be confrontational if/when there is a problem, especially women. Both of the above posters seemed to be surprised the first time they ran into tampo where a woman will refuse to talk to you for a while for some slight they perceived. We would call it giving someone the silent treatment. Sometimes the guy will have no idea what is wrong and is expected to just know what they did wrong. Getting out of this purgatory usually involves assuring the woman that what you did you are sorry for. After some period of time, all will be forgiven and she will go back to normal as though nothing has happened.
3: Construction materials are different. In the United States it is mostly wood and drywall on a brick or cement foundation. In the Philippines, there is little wood or dry wall in stand alone houses due to the high heat and humidity would turn that into mush within a few years. Most stand alone houses are mostly cement blocks and painted so they can stand up to the humidity.
Other interesting notes from my own personal communications with people in country:
A: One person I was talking with mentioned a number of settlements built after some of the typhoons in the area around Ormoc. Some of those places are still without electricity but the people do have cell phone service and are able to have lighting with small solar cells or charge phones from a place of work. One person that I know was able to send me reports during a recent typhoon as it passed over the city one night in 2016.
B: Some of the construction did not stand up to the recent earthquake. (Ormoc 6.5 on the scale) I had a chance to review some photos of damage to a house with concrete block walls that were holding up a main support beam in the center of the house. The area of the walls under the beam held at both ends and they were able to effect some repairs on the wall. I tried to see if there was something else that could be done to shore up the wall or additional added as a safety for the beam in case one end failed but had not seen anything that looks like it would be much better than what is already there.
C: The exchange rate prior to 2007/2008 was about 50 PHP to 1 USD, fell to about 40 PHP to 1 USD around the debt ceiling problem in 2010 but has been getting better for the USD where now it is getting over 45 PHP to 1 USD. Normally, I would not watch that too much except the second person (Exciting Cebu) made multiple mentions about how the weaker USD made his retirement much more expensive than at the start.
D: Many locals do not seem to understand gross margin for businesses operations. Basically, in the US most people understand that if you sell inventory, you need to make sure that you are replacing it so you can continue to operate. For whatever reason, many people in country seem to just view that the money can be spent on 'whatever' and do not seem to realize that they need to replace inventory in order to remain in business. The first poster talks about this observation in a few videos about different businesses he considered plus the problem that when anyone seems to get a business going, four more spring up around it and then everyone is losing money because there are too many people in business.
E: People getting scammed, especially guys. I have no idea why, but the first guy reported in one of his videos of something like 5 or 6 guys buying their Philippine 'girlfriend' a house for something like $15K to $20K. Of course, the problem was that they were dumped immediately afterwards and out the money, with no legal recourse. Life Beyond The Sea's reaction almost seems to be "Guys, come on, what were you thinking?" and he even seemed exacerbated about getting multiple reports.
F: There is an element that will try to con you. I had a friend that came back from a south east Asia trip and was in Manila October 2016. He reported that 'he felt he needed to make sure someone didn't steal his watch off his wrist'. My impression from other reports is that the outlying areas have people feeling safer than large cities.
G: The purchasing power is a lot better for some things, and there is some discussion as to holding the locals to a local price or being willing to pay up a little to get better service or make everyone feel better (some people may refer to this as the kano price). I traveled to Lughansk Ukraine in 2001 and my view is that I wanted the people I had with me to have a vested interest to make sure things went well and there was no problem with my trip, so I paid up for some things like having a translator available during most work hours. It didn't cost that much at $100 USD for three or four days. I could have probably gotten away with only $20 in total since the average salary was around $200 USD per month then, but for me it was much less than what I would have paid in the United States so I was happy with the price, and it was more than she could have made working any other job instead of working for me for 3 days.
It is a fine balance where one does not want to come off as looking like they are showing off and buying friends AND does not want to look like they are chiseling the locals down to the last cent by taking advantage of their less economic activity. My view is that one should try to pay up a little and be seen as the gracious or magnanimous host, where, yes, you probably do have more money than most of the people you run into, but everyone is your friend and one does not disparage ones friends just over a difference in wealth.
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