Let's encrypt installer fails on Ubuntu 16.04

Is this a system with a small amount of RAM available by any chance? You might be running into this issue:

Possible workarounds include adding a swap file, using the letsencrypt package in Ubuntu (which comes with a precompiled python-cryptography package, so it doesn’t suffer from this problem, but it’s slightly outdated, though probably “good enough”) or using a different ACME client.