Just some general advice for the moment:

Always, and this means ALWAYS use strictures at top of the program:

use strict;
use warnings;
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If you do not understand messages produced by use warnings you add use diagnostics; and later on commenting it.

Doing so you are forced to declare variables, and doing so you are forced to think about the visibility scope you give them. So;

# $item_date = "DATE";
# becomes
my $item_date = "DATE";
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Then prefere and use lexical filehandle instead of bareword ones (anyway bareword form is used UPPERCASE). Always put the mode for opening even if < can be omitted. Check if the operation succeded. Always close explicitly your filehandle when you do not need them anymore. So:

# open (file_read, "input-checkbook.txt");
# becomes
open my $read, '<', $filepath or die "impossible to read from [$filepa
+th]!";

..

close $read;
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You can use autodie; if you want to write less.

After all this important things even if not pertinent to your problem.. it is by far better to reduce the code you sumbit for review to isolate the presumed error you encounter..

My time is finished for now..

welcome!

L*