It has been suggested to me that I can manage all eight with one certificate using Subject Alternate Name (SAN) but I have not been able to find instructions specific to my scenario.
I am using GoDaddy but NOT paying them for SSL, so using the GoDaddy cpanel is not an option. I am instead using SSLforfree in “manual verification” mode. I have to redo this every 90 days, which is easy for one certificate, much more annoying for 8 certificates. How can I use the SSLforfree manual verification method to setup one certificate that covers all 8 of my domains? If SSLforfree CAN’T do it (for free), is there something that can?
No, they’re all separate challenges from Let’s Encrypt’s perspective. Every tool you find will have the same requirement. Usually it doesn’t matter because you’re supposed to use tools that do this for you.
I could swear that at some point I managed certs out of the root .well-known/acme-challenge/ folder (the root of the storage area, below even the main domain). However I don’t seem to be able to do that now. I know I did at one time because I did not have .well-known folders in any of my other domain folders that I previously created separate certs for.
Another workaround is to put all of your domains on the free Cloudflare plan (proxied, you’ll see what I mean if you try it), then they allocate the certificate for you.