This is kind of a test post to make sure that everything is still working. I'm always a bit hesitant to update the site because I really don't have time to fix things if anything breaks. I know I can always roll back to a previous version but the fact that things were broken would bother me more than knowing that things are just out of date. That said, the security vulnerability warnings were what finally got to me. If I was running wordpress I'd be more proactive but orchard cms is obscure enough that I hope I don't have to worry about mass portscans and automated site takeovers and the like.
A note for future reference, the couple of problems I did run into during the upgrade was not .net related but when I created my database admin account I gave it too much power (I think by putting it in the sys admin group) so the default schema for that account was getting overridden by dbo and therefore it wasn't automatically seeing all of my orchard tables when I tried to restore the DB to a local instance.
The main symptom was that every time I started the app in my local dev env orchard would ask me if I wanted to create a new site, even though I'd already set the default schema for the account to the appropriate value. I was able to eventually fix the problem using old fashioned rubber duck debugging. Since the only difference in the codebase was the connection string the problem must have been on the DB side.
The other issue, in a similar vein, I needed to create a login for my orchard db admin, and then map that user to the actual db user account. My description here is kind of sketchy but hopefully it'll be enough whenever I next decide to work on this site!
Another editor note: I had to fix the image thing again which tells me that this is a deployment issue I need to fix.