You could search for and delete the token then insert the new text

#!perl
use strict;
use Win32::OLE;
use Win32::OLE::Const 'Microsoft Word';
$Win32::OLE::Warn = 3;
my $word = Win32::OLE->new('Word.Application', 'Quit') or die;
$word->{Visible} = 1;
$word->{DisplayAlerts} = 0;  

my $doc = $word->Documents->Open({FileName => "c:/temp/Word.doc"});
my $sel = $word->Selection;
$sel->Find->{Forward}        = 1;
$sel->Find->{MatchWholeWord} = 1;
  
for my $n (1..2){
  $sel->Find->{Text} = '##TOKEN'.$n.'##';
  $sel->Find->Execute;
  $sel->Delete;
  $sel->InsertAfter("($n) This is line 1 of some new text that is more
+ than 255 characters.
This is line 2 of some new text that is more than 255 characters.
This is line 3 of some new text that is more than 255 characters.
This is line 4 of some new text that is more than 255 characters.
This is line 5 of some new text that is more than 255 characters.
This is line 6 of some new text that is more than 255 characters.
This is line 7 of some new text that is more than 255 characters.
This is line 8 of some new text that is more than 255 characters.");
  $sel->MoveDown({Count=>1});
};
$doc->SaveAs({FileName => 'c:/temp/Word1.doc'});
$doc->Close();
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