One key factor I have not seen mentioned for whether or not the Roxana proposal will pass is how many schools without 11-man football will participate in the vote. I believe their votes were a deciding factor when districts were passed in 2018 and certainly can be again.
When districts passed, the vote was 324-307 in favor, which was less than a 3% margin. Even if you assume every team that played 11-man football at the time voted, at least 11% of the votes came from schools that did not participate in the sport. There is no way to be for certain how the schools without 11-man voted but it seems fair to assume they heavily favored districts (and will again favor Regionals) for several reasons.
First, most if not all schools without 11-man are much smaller than the average IHSA school. The prospect of 1A schools being able to play other 1A schools would seem appealing if you have a tiny enrollment yourself. Some smaller schools may have recently moved to 8-man but are thinking they could make the switch back up to 11-man if they were protected by Regionals, which would give them more reason to vote in favor of it.
Second, it seems fair to assume schools without 11-man are less competitive in sports (which can at least partially be attributed to smaller enrollments). Because of this, it’s harder to see them joining the train of thought that 3 and 4 win teams do not “deserve” a playoff spot.
Third, instituting Regionals/Districts would remove the impact of 11-man football on conferences in other sports. There are some ADs around the state who do not have 11-man football but have to deal with conference jumping/realignment because of it. From their perspective, 11-man football is a nuisance causing them problems and getting rid of football conferences would resolve the issue permanently.
There are more IHSA voting members without 11-man football now than there were in 2018, so their potential sway has only gone up since then.