It does give him an advantage, because BB chooses to not put everything into the top 5 or 10 players, while leaving the rest for scrap.
The more players on a roster, the more depth teams have, ie the less valuable each roster spot is. This makes managing players easier, and overcoming bad signings easier as well. Since BB seems to be better at managing players than most, a larger roster would lessen the advantage he gets from this.
You are probably right because BB does not seem to want a larger roster size.
But I still don't really understand it. I would think that a deeper team would have better players at the bottom of the roster and thus more to lose than a top-heavy team that has only easily replaceable players at the bottom.
One good example of the "use them or lose them " result from the current roster size is Danny Woodhead. With a larger roster size, he might be buried on the depth chart in New York rather than a star here. In that case, the roster size worked in our favor.