I have really been trying to wrap my head around this one. On one hand you have a team that does not belong in Henlopen North in football. However, they have won championships in other sports. I guess the question becomes, who controls the conference. Last time I checked, it is indeed the conference. The DIAA has gone on record saying the conference can do what they want. Specifically with how Poly and Milford were counting numbers a few years back.
The way I see it football can play in the South, but here is the rub. Because of their enrollment numbers they would be ineligible to participate in the D-II tournament and classified as a D-1 team. Depending on how well they did during the season, this could cost the South a playoff birth, if Poly did well. But if that is a risk the conference is willing to take, they should be allowed to. Maybe this could be the impetus for the DIAA to take a hard look at how they are classifying the teams in various sports.
It's been past time to classify based on talent instead of enrollment. Delcastle/Wilmington Charter/Poly were never going to be football powers and schools like Woodbridge/Delmar/Caravel/Howard/Friends could certainly compete at a D1 level. Some schools are just good/not good at certain sports, enrollment or not. DIAA needs to look into it once they settle the office.