Topper, whether you are a pilot or an ATC, throughout all your traning, you go through checklists, get readbacks, and generally tinplate your arse. Why do we all do that, because in this game their are quite often no second chances.
The risk may be small that in that jump through E airspace, the 737 may clean up that VFR, but as I said above, it has always been drummed into us, any risk, no matter how small, is too much of a risk. We are all being asked to take a small risk, and told to accept that as an economic reality. Well thats just not good enough.