It is to some extend self explanatory. Perhaps you can
easily rearrange the output from the structure.

#!/usr/bin/perl

use warnings;
use strict;
use Data::Dumper;

my @data = <DATA>;
my $struct;
my ($case, $table, $man, $seat, $round, $who, $what);

for (@data){
   /^\s*$/ and next;
   /^\s*#case\s+\w+:\s+(\d+)/i   and $case  = $1 and next;
   /^\s*people\s.+=\s*(\d+)/i    and $table = $1 and next;
   /^\s*round\s+(\d+)/i          and $round = $1 and next;
   /^\s*seat\s+(\d+):\s+(\w+)/i  and ($seat, $man) = ($1, $2);
   /^(\w+)\s+(.+)?\s*$/          and ($who, $what) = ($1, $2);
    
   $struct->{$case}{$table}{'seat'}{$man} = $seat if $seat;
   push @{$struct->{$case}{$table}{'round'}{$round}{$who}}, $what if $
+round;
}

for my $case (keys %$struct){
 for my $table (keys %{$struct->{$case}}){
  for my $round (keys %{$struct->{$case}{$table}{'round'}}){
   for my $man (sort keys %{$struct->{$case}{$table}{'round'}{$round}}
+){
      print "player: $man  ";
      print "case: $case ";
      print "seat: $struct->{$case}{$table}{'seat'}{$man} ";
      print "round: $round ";
      print "QA: ", join '. ', @{$struct->{$case}{$table}{'round'}{$ro
+und}{$man}}, "\n";
   }
  }
 }
}

#print Dumper($struct);


__DATA__
#Case Number: 12345
People at table = 5
Seat 1: Joe
Seat 2: Steve
Seat 3: Mary
Seat 4: Jill
Seat 5: Bob
Jill speaks first
Round 1:
Jill says good
Bob doesn't talk
Joe says bad
Steve says good
Mary doesn't talk
Jill says that's enough
Mary talks for years
Steve says that's not enough

Round 2: Next question
Jill says bad
Bob doesn't talk
Joe says bad
Steve says bad
Mary doesn't talk
Bob says that's enough
[download]

Which has the following output:
player: Bob case: 12345 seat: 5 round: 1 QA: doesn't talk.
player: Jill case: 12345 seat: 4 round: 1 QA: says good. says that's enough.
player: Joe case: 12345 seat: 1 round: 1 QA: says bad.
player: Mary case: 12345 seat: 3 round: 1 QA: doesn't talk. talks for years.
player: Steve case: 12345 seat: 2 round: 1 QA: says good. says that's not enough.
player: Bob case: 12345 seat: 5 round: 2 QA: doesn't talk. says that's enough.
player: Jill case: 12345 seat: 4 round: 2 QA: says bad.
player: Joe case: 12345 seat: 1 round: 2 QA: says bad.
player: Mary case: 12345 seat: 3 round: 2 QA: doesn't talk.
player: Steve case: 12345 seat: 2 round: 2 QA: says bad.