I can only add to the chorus here. Recently used LE to generate certs for my servers running on FreeBSD, which to date is really only semi-supported by LE.

To my surprise, getting certs was quite easy. Just needed to run the LE utility, answer a few questions, like the domains to be included, and that was it. Took a few seconds at most.

The only other task was pointing nginx servers to the LE certs location, edited the config files in a minute or so. Of course that only needs to be done one time.

Using the early-stage LE tools is already quite painless, I expect fully automating the process will be developed in the coming months. But even with the "primitive" tools available now, it's hardly a burden spending a few seconds every 3 months to get the tremendous benefit provided.