[More Cowbell]

This second one looks pretty balanced except for the 60th which would really only be a 3 team district.

What would be wrong with this:

57th
Paintsville
Johnson Central
Magoffin Co.
Lawrence Co.

58th
Allen Central
Prestonsburg
South Floyd
Piarist

59th
Pikeville
East Ridge
Shelby Valley
Pike Co. Central

60th
Belfry
Phelps
Sheldon Clark
Betsy Layne

Unless you bring in another team from another Region, this seems fair to me.

The second alignment still seems to have the same problem as the first one, except that the 58th becomes the "3 team district" instead of the 60th. And I don't think they would move Betsy Layne out of the 58th just to move Piarist in.

Really, if you assume that Piarist may or may not field a team next year, you only have 15 teams for 4 districts, meaning some district is going to only have 3 teams. The only way to rectify this is to steal a team from another region.