Having the DNS credentials laying around on the server is not a good idea. So creating wildcard certs via letsencrypt is a huge pain in the ass.
If a webmaster has control over somedomain.com I think that is enough to assume he has control over *.somedomain.com. So I think letsencrypt should allow wildcards to the owner of somedomain.com without dabbling with the DNS.
The way things are now, I don't use ssl for my smaller projects at smallproject123.mydomain.com because I don't want the hassle of yet another cronjob and I sometimes don't want the subdomain to go into a public registry (where all certificates go these days).