automation will eventually be the way just that Letsencrypt client and 3rd party clients need time to evolve and develop to the stage that is acceptable for most folks

there's a list of clients being developed on their forums some already have auto renewal automation done

see

https://community.letsencrypt.org/t/list-of-client-implement...

for plesk https://community.letsencrypt.org/t/plesk-and-letsencrypt/42...

for Centmin Mod LEMP stack http://centminmod.com/letsencrypt-freessl.html

cpanel feature request at https://features.cpanel.net/topic/provide-support-for-lets-e... where cpanel folks are interested too