I am an expat myself and I love this country, I came here 2 years ago, the weather here is the best in the world, only a bit rainy in the winter but no hurricanes what so ever.
However in my case I initially got a property in Escazu, right on the central Valley to have a feeling of how life is on this part of the country.
It was a very good choice because I got a good deal and I sold my house just when I wanted to do so.
Eventually I moved to San Ramon which is an amazing area! Very calm. Secure and relaxing and just breathtaking views, I can see the ocean from my home!
And we have a lot of Expats friends from all around the world!
I also got a small property in Jaco as an investment.
As for the medical, it is way more cheaper here than back home so I don’t think you need to worry about prices.
I had this amazing people helping me out with all of my relocation and property buying, they really work the extra mile with me because I wanted to see everywhere before buying! if you want to check them out they really took care of me!
Their website is http://www.internationalrecr.com/ check them out! I am sure they will make the whole process easier.