Some of this is funny, if Dresden's principal is so powerful why didnt he just create a district with all the easy teams and put all the good teams in another? The reason is that the districts are based on where the towns are geographically. The single a districts now are the exact same as the were in the early 90s with huntingdon, uc, and humboldt added.
As for Dresden's classification, in the 1999 season dresden went 2a in the district with uc, humboldt, trenton, gc, and halls. Dresden struggle for a few years. A couple of years later milan and westview came into the district and in the2003 season dresden finished 2nd behind milan and made the playoffs again in 04. The losing streak occurred during the 07 & 08 seasons when dresden was in the same district. In 2009, the tssaa went from 5 classes in football to 3 classes for all sports in the regular season and 6 classes in the playoffs for football. At this point dresden went to1a in the regular season and 2a in the playoffs. The link you provided does show dresden in 2a but so is milan, westview, etc. those teams are now 2a in regular season and.3a in the playoffs.
I thought this might clear this up. If you think it is wrong. Just go and look at the schedules from those years on coacht, im sure they are still up so you can look at them.
Ill say it again the hodges are very good coaches! But if dresden was playing in the district with milan, westview, crockett, obion, etc they would be about where they were in the years when they were playing in the district with those teams.