1: Check for data in Text widget -there are other ways, but I think this is the most efficient.

use Tk;

my $mw = MainWindow->new;
my $text = $mw->Text->pack;

my $bFrame = $mw->Frame->pack(qw/-side bottom/);

$bFrame->Button(
   -text => "Check Text",
   -command => sub {
      if ($text->index('end - 1c') == 1) {
         print "Text is empty\n";
      } else {
         print "Text contains data\n";
      }
})->pack(qw/-side left/);

$bFrame->Button(
   -text => "Clear Text",
   -command => sub {
      $text->delete("1.0", 'end');
})->pack(qw/-side left/);

MainLoop;
[download]

In your sub it looks like you want something like:

   if ($text->index('end - 1c') > 1) { ... }
[download]

As for 2, It looks to me like "right" and "left" set margins -- they are not intended for wrapping text. You probably want the break option, which can support break_wrap, break_at, and break_TeX. It looks like break_wrap might be what you're looking for. Also check the Text::Reform module (which Autotext uses) for more info

Rob