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We actually used a virtually identical system.  We knew we wanted to retire in Europe (we are from the US). So, over the course of several years, we traveled a lot, especially to places that we felt were "possible" retirement destinations.  We started off with 3 simple criteria in selecting those possibilities -- cost of living, weather, and a medium to large city, as they are all very important to us.  We knew we wanted to live somewhere temperate/warm, and we wanted to make sure it was affordable to live a lifestyle we wanted.  We wanted the medium to large city for the purposes of convenience, living a true EU "urban" lifestyle, and convenience to live without a car.

So, once we knew those 3 things, we started traveling to destinations that possibly "fit".  Before starting I made a spreadsheet of criteria that mattered to us -- cost of living, weather, quality of public transportation, ease of learning the language, safety/crime, food, culture & friendliness of the people, ease of access for travel back to US and to the EU, quality of green space, and a few others.   Not all are as important as others, so we weighted them accordingly -- example, cost of living was on a 10 pt scale, weather was on an 8 point scale, language was on a 5 point scale and ease of access for travel only a 3 point scale.  This was based on their level of importance to us, not on anything else.

Anyway, many trips later and Lisbon was our top ranked city, with Valencia, Spain being a relatively close second.  Final decision was made my taking a trip to BOTH cities back to back.  We realized upon ending that trip that as much as we liked Valencia, we "missed" Lisbon more each time we left. 

So, that was our system -- quite methodical and data driven, but supported by our love of the people, culture and city.

To me it was somewhat spontaneous. I'd spent a month in Lisbon back in 2014 and left nearly in tears because of how much I'd enjoyed it. When I figured I'd had enough of life state-side, I knew exactly where to go.

Yep, each time we left, we felt overwhelming sadness, unlike how we felt when we left other cities.  That told us a lot.

Hello nyyfan30,
are you actually living in Portugal now or still in the US? If you are already here, have things worked out as planned for you? We also had a look at Valencia, which we think is a very good place as well. Very flat and good surfaces for easy walking.

Tom,

Unfortunately, not yet.  We are moving in August.  We were hoping for last year, but COVID sort of made us delay our plans until it made more sense from a health standpoint.  Now, we are very eager to move and have started the planning, visa process, etc.   These next 5 months will hopefully go by very quickly, although it seems like a long time at the moment!