It attempts to make an autosave upon entering the Strip, but the file is always corrupted. Thinking that the issue was related to the autosave feature, I completely disabled autosaving, and tried the transition again. Still got the black screen of fun-killing.
I have done some digging on the internet, and have discovered that others have had this same problem when preforming the quest "I put a spell on you", the one about the Legion turncoat at Camp McCarren and the monorail bomb. In my game, the Monorail did not survive the quest, and I think that has something to do with it, though I have also been doing a lot of other crap since the last time I set foot in the strip, including some companion quests.
Wondering if anyone else has encountered this problem, if they know how to fix it, so on and so forth. And no, I do not have any saved games before I started the I put a spell on you quest. Hooray for expecting the worst!