I think this type of service is best implemented further down the chain. The possible configurations are so complex and in many cases so technical, that even with hand-holding, it would be very difficult to offer a level of support sufficient to the need, especially at no cost to the user. Not to mention issues with liability when the advice/help inevitably causes damage.
Luckily, common web control panels are now offering dedicated modules for using LE, making usage of the service as simple as a few clicks. We already have support inside cPanel and Plesk. Many hosts with custom software are beginning to include support for LE. At least in my mind, it is probably better to direct energy in integrations and automations for other common products. That will give the best results for the effort expended.
If someone is managing a server manually, they should already have enough knowledge that some guides would be perfect for their skill level. Having some easy-to-find guides on generic configuration and conversion to common formats (jks, for example) would be perfect for this set.