I assume this is either difficult or impossible for the

Question

I assume this is either difficult or impossible for the

compiler team to implement for some reason.

No, it is not at all difficult or impossible to implement -- the fact that you implemented it yourself is a testament to that fact. Rather, it is an incredibly bad idea and so we don't allow it, so as to protect you from making this mistake.

call to Monitor.Exit within ExitDisposable.Dispose seems to block indefinitely (most of the time) causing deadlocks as other threads attempt to acquire the lock. I suspect the unreliability of my work around and the reason await statements are not allowed in lock statement are somehow related.

Correct, you have discovered why we made it illegal. Awaiting inside a lock is a recipe for producing deadlocks.

I'm sure you can see why: arbitrary code runs between the time the await returns control to the caller and the method resumes. That arbitrary code could be taking out locks that produce lock ordering inversions, and therefore deadlocks.

Worse, the code could resume on another thread (in advanced scenarios; normally you pick up again on the thread that did the await, but not necessarily) in which case the unlock would be unlocking a lock on a different thread than the thread that took out the lock. Is that a good idea? No.

I note that it is also a "worst practice" to do a yield return inside a lock, for the same reason. It is legal to do so, but I wish we had made it illegal. We're not going to make the same mistake for "await".