Thank you for your reply DanSchaper!
Unfortunately, editing the /etc/lighttpd/external.conf as directed to in the large warning block resulted in nothing but errors for me. I found this thread that states that changing ports aren't handled well currently, and I chalked it up to that.
I do agree, I should add a note about that in my solution though. There is a reddit post here where a user shows a quick command to update the port after an update of PiHole.
If you have confirmed editing the port in the /etc/lighttpd/external.conf file works for you, do you think I could pick at your brain a little?