I started looking into the Portugal mainland about 4 years ago but wasn't ready to make a move then as I was waiting until I had Social Security and my Motorola pension. I finally decided to go there to check it out in May last year but Covid came along. I had wanted to go to the mainland for 10 days and 3 days in the Azores. I don't want to live in a big city like Lisbon and couldn't afford it if I did. I am not much into nightlife or bars and am pretty much a homebody. I had a few areas I had researched as possible places to live.and wanted to check them out. But in the last 4 years houses in those areas have mostly gone up more than I can afford. I will have about $150k US from the sale of my current house. I plan on renting for a while to make sure I picked the right area etc. I need a detached house because my main hobby and stress buster is music so I don't do well in flats or semi's. 😀 After doing a lot more research most of the places I found were inland and to isolated even for me. 4 years ago I could find nice looking places in my price range in the Algarve and places north of Lisbon but not any more. I don't need an especially large home as its just me and 2 cats and after owning a 5000 sf Victorian I don't want to have a large house to clean, furnish and maintain anyways.
So on to why I am making the Azores my first choice. First it seems cheaper in general to live there than the mainland. Also the VAT taxes are less there. I can still find houses there in my budget that seem ok. I love nature and love to walk and hike etc so I hope it will help get me out of the house more with all the natural beauty to experience. If I have reservations after I visit there I will likely visit the mainland and see what I can find.
I was surprised that the rainfall in the Azores was 30 to 40 inches a year depending on which island. The town I live in now gets 45 so I don't think that will bother me. Also the moderate temps will make up for it.
One problem I will have is that my vision has been deteriorating and I may not be able to drive for to many more years so I will also need to be near public transportation.