Finally got to implement Lets Encrypt on my personal server. It feels good to transition from StartSSL to the free Lets Encrypt. I was able to use this on my Apache, Postfix and Dovecot installs.
I also setup a crontab entry to renew the cert every two months.
I am thinking of moving my main server to FreeBSD. My main goal is to learn the OS. I have gotten so use to Debian and It seems like it is no longer a challenge to me. At least I think with #FreeBSD, I do not have to worry so much with upgrading. Right now, since I track Debian Unstable, I have to constantly update when I am in there. Also I also have to update the kernel. All of this I know are avoidable. I could just go with Debian stable and I could just choose to use the distro kernel and not have to worry with compiling the kernel.
Anyway, I think this would be a huge undertaking. I probably would have to plan this in stages. For one, how do I migrate without significant downtime???