Dear JP,
there is a lot of construction going on outside of San Jose especially in the Guanacaste area. There is a boom and several companies from the San Jose area are coming to Guanacaste. Some of them are very good and professional others are not. I would say especially your management skills and your language can help you a lot. I don´t want to say your skills are better than the ones from the Ticos, there are very well organized and English speaking ones, but because of the boom right now, they are unable to cover all what is going on.
Be careful, it is a different country and you have to be very flexible regarding the way of managing, some thinks are very different here and you might have to be a student again and put beside what you used to do and the way you did it.
There are many North Americans comming to invest, some want to built their home or project. There is a lack of good skilled English-Spanish speaking supervisors, to communicate between the builder / contractor and the owner / purchaser of the home. I would recommend you to try to connect first with a company /builder in order to learn the system and then go from there.
In the US there are Home inspections, here there is hardly anyone who can do a reliable inspection with a good report.
Regarding your child or future children you might want (or have) to stay close to San Jose because of the schools. In more remote areas like on the beaches the quality of the schools is not what you might expect. Except the country day school between Tamarindo and Flamingo.Country Day School. see:
http://www.cdsgte.com/Hope I could help a little, good luck