I got a lot of new info:
Calendar is now working, mostly. Here’s some bullet point details.
-Had to change owner recursively on the plugin to www-data:www-data to get it working. I tried www-data:wp-user once, but it couldn’t write to cache that way. I deleted completely to test if the chown settings fixed it, and got caught in that loop where I couldn’t install the plugin. Doing so from the dashboard would show me the dashboard sidebar, but an empty content area (as it did yesterday). I manually uploaded via ftp, and it showed again.
-I changed the owner to www-data:www-data, and the plugin activated properly.
-I now get the an error that the plugin cannot write to robots.txt, looking into this.
-Despite deleting EVERYTHING, my Event Categories remained (might want to make sure they get cleaned up?). Oddly enough, they only saved the name, and slug, the color / pictures to represent them were gone.
I run every other plugin on my site (to my knowledge) with owner wp-user:wp-user. I do believe W3 (not activated) may have required wp-user:www-data, or www-data:wp-user, but I can’t recall. That being said, nothing has ever required www-data:www-data, so this is odd to me.
I’m still doing some testing now to iron out any kinks, but I figured this info would be useful to you. It definitely seems like there are some new permission errors going on, but I can’t be sure.