But I am sure things will change soon, just like everything is changing so quickly in the IT field
The automated certificate management that LetsEncrypt utilizes *is* the change you're waiting for! Prior to that, you had to learn how to use OpenSSL to create a CA, generate a CSR, get it signed (or self-sign), and finally install the resulting files (along with an intermediate certificate chain file in some cases) onto your server and edit your Apache config file(s). Windows wasn't much easier, but AFAIK you can only install the Microslop CA on a Windows Server OS.
All of my certs at work are due to expire in August, and the last time I had to rotate certs it took me 32 hours and mandatory service restarts or server reboots on every system in the farm using HTTPS/SSL. Not looking forward to July for sure, although I may look to see if I can borrow any of the LetsEncrypt automatic distribution logic (even though I can't use their certs for auditor reasons) to simplify the next round of upgrades.....