Since this seems to be fixed-width columns, I'd probably go with tilly's suggestion of unpack. Here is a stab at a regex solution that I'd probably not use:

#!/usr/bin/perl -w
use strict;

# First, we will allow no digits anywhere in a name;
# this will allow us to detect the extension after the
# name.  Second, we only allow single spaces in a name
# (and can't start or end with a space).  Third, names
# must contain a comma (but not in front).
my $name= qr{
    (
        [^\s\d]
        (?: \s?[^\d\s]+ )*
    ) , (
        (?: \s?[^\d\s]+ )*
    )
}x;

# Org can only have single spaces and no commas, but is optional:
my $org= qr{ (?: [^\s,](?:\s?[^\s,]+)*[^\s,] )? }x;

# Heading must have "-" on each end and just one word between:
my $head= qr{ -\s+[a-z]+\s+- }ix;

my $entry= qr{
    \s*
    (?:
        $head
    |
        $name \s+ (\d+) \s+ (\S*) \s+ ($org)
    )
}x;

#print "$entry\n";
while(  <DATA>  ) {
    my @matches= m/^$entry$entry\s*$/;
    #print "$_";
    for(  [0..4], [5..9]  ) {
        my( $last, $first, $ext, $room, $org )=
            map { defined $_ ? $_ : "" } @matches[@$_];
        if(  "" ne $last  ) {
            print "($last), ($first) ($ext) ($room) ($org)\n";
        }
    }
}
__END__
NAME              EXT  RM#    ORG       NAME              EXT  RM#    
+ORG     
 -------------------------------------   -----------------------------
+---------
 - A -                                   BASILE, YYYY      5555 1H08  
+ IAMG    
 ABEND, YYYYYY     5555 2014   CE        BATES, YYYY       5555 4832  
+ BT      
 ABRAMS, YYYYY     5555 C-07             BATHERSFIELD, YY  5555 B-39  
+ CE      
 ADAMS, YYYY       5555 255    OTC       BAXTER, YYYY      5555 A-43  
+         
 ADAMS, YYYY       5555 149    BT        BEAR, YYYYYY      5555 H42   
+ ATO     
 ADAMS, YYYYYYY    5555 A-16             BEASLEY, YYY      5555 D-79  
+         
 ADUAKA, YYYYYYYY  5555 A-52             BEATTY, YY        5555 4832  
+ TAG     
 AHMED, YYYYYY     5555 C-63             BECHTLE, YYYY     5555 D-26  
+         
 AHMED, C. YYYYYY  5555 D-69   SOMEU     BEDOYA, YYYYYYYY  5555       
+ CE
[download]

Which prints the following:

(BASILE), ( YYYY) (5555) (1H08) (IAMG)
(ABEND), ( YYYYYY) (5555) (2014) (CE)
(BATES), ( YYYY) (5555) (4832) (BT)
(ABRAMS), ( YYYYY) (5555) (C-07) (BATHERSFIEL)
(D), ( YY) (5555) (B-39) (CE)
(ADAMS), ( YYYY) (5555) (255) (OTC)
(BAXTER), ( YYYY) (5555) (A-43) ()
(ADAMS), ( YYYY) (5555) (149) (BT)
(BEAR), ( YYYYYY) (5555) (H42) (ATO)
(ADAMS), ( YYYYYYY) (5555) (A-16) (BEASLE)
(Y), ( YYY) (5555) (D-79) ()
(ADUAKA), ( YYYYYYYY) (5555) (A-52) (BEATT)
(Y), ( YY) (5555) (4832) (TAG)
(AHMED), ( YYYYYY) (5555) (C-63) (BECHTL)
(E), ( YYYY) (5555) (D-26) ()
(AHMED), ( C. YYYYYY) (5555) (D-69) (SOMEU)
(BEDOYA), ( YYYYYYYY) (5555) (CE) ()
[download]

Finally, $name =~ /\U$name/; doesn't do anything useful. You want $name= uc $name;.

        - tye (but my friends call me "Tye")

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