Well, Tim definitely enabled her to an extent whenever she exhibited fear, i.e. driving, working, etc. Heck, he even told her once that "he was the man, and he'd take care of her." in response to her anxieties about those things. In doing so, he has created the situation she's in, to an extent. And let's not kid ourselves - she loves it.
I try not to judge others levels of anxiety too but I know from firsthand experience that all too often, people say they experience things to such an exaggerated level when they really have NO idea what it is REALLY like to experience full-blown panic attacks enough to land you in the ER multiple times.
As a side note, I also get migraines. Have been getting them for 25 years. Absolutely have ruined fun outings for me, taken me away from special days of celebration in my family, made me lost umpteen days of work, always sit in the back of mind "if" I'm going to get one on a particular holiday (which I have), physically sick with intractable vomiting, weak and exhausted from not eating, hurts to talk, hurts to move, etc. The whole 9 yards.
So when people have a tension headache and they complain - dramatically - that they have the WORST
migraine, but then go about their day eating, working, visiting and chatting with people, etc. Well, you can see that I want to punch them the f$ck out.
That's kinda how I see the situation with Jenn. Initially, I felt sympathy because I knew those feelings all to well. But when you end up seeing - over the course of many years - that anxiety turn on / off and crop up at the "right" moments or go magically away at others, then you start to get skeptical.
An example - remember when they said they don't like to meet people in the parks because they're anxious and antisocial and get unnerved with everyone coming at them? How about that meet-and-greet they did that was well-documented on Twitter a few years' back at MNSSHP? It was a literal LINE of people forming to meet them. Guess it turned "off" that night.
Sorry for the rambling...