St. Bonaventure played a very similar schedule last year with games again Jackson St., MD Eastern Shore, and Siena (all around 300 RPI or worse), they played an Ivy League school in Yale at home, CAA opponent Northeastern (who has recently been similar in strength to W&M), they also played at home to Vermont, an unexpectedly great mid-major in Buffalo (25 RPI), a couple of middling mid-majors (Niagra, Canisius), a mediocre P5 team in UMD, and then Syracuse and TCU.
They finished their OOC at 11-2, even lost their first game at home to Niagra, and no one thought they were going to get an at-large (mostly because they lost to Niagra), but a really great run in conference play put them right into the conversation, and that was in a down year for the A-10.
I think people need to realize that it is not quite make or break in the OOC in the same way it was when we were in the CAA.