@slausonbeanco
Very smart. Come here first... no strings attached. I like your plan.
What TerrnViv wrote is really good information. Only you know you... and since you haven't been here yet, you will be surprised!! The microclimates are sudden and can happen even during a 'hike' up into the local hills... the 'land' and the 'clouds' are a lot closer here than in other parts of the world. You can walk in a cloud forest.
I too thought I'd be near a beach. Barefoot, sleeping in a hammock, dozing half naked with a sweaty bottle of beer and my pet monkey under the roof of our open-air, tiki hut with 'Gilligans's Island' written all over it... I was dead wrong. The coast was expensive, hot, and many places were not a good, 'comfortable' distance from hospitals. The 'emergency' travel time would most certainly be death for me in some of those places. Remember... the ambulance has to travel TO YOU first; and then find you (we don't have addresses in much of CR) and then get back to the hospital before you are dead. Most ambulances do not have medics. ???
I live 45 minutes south of La Fortuna (town) and go there for the occasional aimless afternoon of shopping and drinks or to the natural hot waters. The lake is very pretty and I would love to live in the hills overlooking it... but the 'for sale' signs up there were all in English... thus, it was going to be all Gringo Pricing and I didn't want that for me. I opted for a tiny village south of Fortuna, near the main highway; I can take a bus (I don't drive) and go to Fortuna, Quesada (city with everything) and San Ramon...where there is also everything you need and easy access to airport (SJ). The area is full of rivers, both big and small, so finding a swimming hole is easy... there are even thermals nearby that are far cheaper than anything in Fortuna. Wildlife is abundant... I ran into a pack of Capuchin monkeys on my morning walk this past week... not normal, but they were fun to see and watch. Such Acrobats!!! Bird life is amazing. This is western San Carlos (canton) and can get from 12-18 feet of rain per year ... so it is wet. But wet means Green and plant life here is jaw droppingly lush and beautiful.
Completely not what I expected to be living in or near... but interesting, and I love it and the people. Once you get away from areas that attract foreigners and even, tourists, the prices DROP significantly. My area has a scattering of expats from all over the world... even Iran; but we are not concentrated nor even organized... we simply 'bump' into each other on a bus, or in the hardware store. Funny... Walmart draws expats like flies... so you can use your old tongue to have a real conversation... and then never see each other again. I sort of like that.
Perhaps make a 'needs' list before you come and see if you can't make some of your stops adhere to that list... you don't want to get seduced into a place that will end up being a struggle with unpaved roads, no hospital, crappy shopping, and hot. That doesn't sound like retirement.
But we are all different.
Best of luck.