What would it take to make this happen? What are the hurdles/roadblocks?

I'd say there would be more issue than a magazine stand.

What would it take to make this happen? What are the hurdles/roadblocks?

 

Frosh season can't run beyond the Varsity season. Season would need to finish one week earlier which means playing one less regular season game or starting earlier.

Personally- who cares. I think it's pretty obvious by the end of the year who the top 2-3 teams are.

All it takes is someone interested enough in it to put it together, organize it, manage the scheduling, etc. It has happened in the past so the schools will buy into it. You leave the last week of games unscheduled until the last couple of weeks in the season. Then you figure out through tie breakers etc. who should be in the title game and match up other schools for their last game off of that.