On best teams ever, I will note that Bedford had good teams in 79 and 80. This was points era and only a four teams would playoff qualify south of Indy large school and Richmond was in that mix. Bedford had good size and tough I heard from older friends. 79 team only lost to East, including sectional. 80 team actually won conference by beating East, but East went to playoffs instead to face Martinsville because Bedford opened season against Martinsville back then.
Since Shelbyville was brought up, their 84 team was strong and tough, very stingy defense. Beat Martinsville and CG (beating them out for cluster) during undefeated regular season. Unfortunately for them, Martinsville edged them 7-3 in sectional rematch.
New Albany was tough matchup in 84 regional for Martinsville, very good team. The 2002 team may be considered top team, beating undefeated defending regional champ Reitz in sectional before getting overpowered in regional at CG on very wet, cold, windy night, which made passing challenging.
Jeffersonville had some good squads in 90's when Bloomington South had many dominant teams.