Fuck Community Server. I guess I didn't close a tag and the rest of my post got cut. Here's the whole story (it's more like a few little WTFs instead of a big one):
The reason I called in the first place was exactly one of our users (the COO, of course) was getting a 500 when trying to log into the hosted Exchange solution we have with the provider. None of our other users (on the same server, mind you) were getting the same error.
So I call and the tech is clueless. His first beef with me is that I'm not an "authorized user" in the company's account, so he didn't want to talk to me. But, I knew the company's credentials to log into the provider support portal, which was where I found the correct phone number to call support. He knew this, and proceeded to give me directions on how to add myself as an authorized user. So I asked him why, if he was telling me how to add myself, he couldn't just talk to me if he knew that I was going to do that. He agreed and said not to do it again. First problem solved, I think.
The next big issue, as I started to explain in the OP, was the IP address. He asked for it, and I gave it, and he was convinced that this was an RFC1918 IP ("You're sure you didn't get that from IPCONFIG, right?"). After he decided that 8. is not the same thing as 10., 172., or 192., he tells me he needs to escalate to level 2. Fine, I tell him, and I wait to be transferred.
Instead, I am treated to the sound of him typing away for a few minutes, with the occasional belly-laugh courtesy of his co-worker (this was after sitting on hold for 15 minutes. Get off Cracked.com and answer the phone, dummie). "What's up?" I finally ask. He tells me that none of the L2 techs are responding in his chat, and he asks me to check the provider's public status page for him to see if anything is being reported. You'd think that even an L1 tech would know where his own status site is and have access to it. Guess not.
Finally, he agrees to call me back (it's been ~30m at this point), and as soon as we hang up the COO calls me to tell me that everything's working. While I'm sitting with the COO the support drone calls me back to tell me that they still have no idea what's causing the problem. I tell him to relax and hung up.
So I guess that story sucked. Fortunately I work at a place where WTFs are pretty uncommon and thus I suck at writing them.
Here's a maybe more interesting one about a Level 3 Communications manager who faked his own death by pretending to drown at Jones Beach on Long Island the other day.