I'm doing a similar project. I prefer to have the sensors report to the cloud and collect the data there. More straightforward for sensors outside my home wifi environment and no need to worry about backing up the server. If necessary you could always have the server pull the data back again. I'm currently using IFTTT Maker but expect to use something more flexible in time.
If you do go for a central server, it depends what you need to do with the data server-side. personally I would prefer the extra oomph of having the pi. For passing sensor data to server, consider MQTT library instead of building your own transport.
The most annoying thing so far on the networking side with the cloud approach has been lack of SSL but totally understandable in a micro-controller.
Espruino is a JavaScript interpreter for low-power Microcontrollers. This site is both a support community for Espruino and a place to share what you are working on.
I'm doing a similar project. I prefer to have the sensors report to the cloud and collect the data there. More straightforward for sensors outside my home wifi environment and no need to worry about backing up the server. If necessary you could always have the server pull the data back again. I'm currently using IFTTT Maker but expect to use something more flexible in time.
If you do go for a central server, it depends what you need to do with the data server-side. personally I would prefer the extra oomph of having the pi. For passing sensor data to server, consider MQTT library instead of building your own transport.
The most annoying thing so far on the networking side with the cloud approach has been lack of SSL but totally understandable in a micro-controller.
I'm going to try the ESP8266-only approach too.