It took me a couple of months to get this to a working state, so I hope that I'm able to save you some time should you find yourself in my shoes at some point in the future!
Uptime and SSL certificate monitoring doesn't have to be boring, confusing or expensive. Together with my buddy Mattias Geniar I'm currently building Oh Dear: a webapp to keep an eye on the health of your websites. Register here to try it out. (sponsored link)