After several days, I finally came upon the solution! By using the id
I already had collected I could call the cluetip function using the
dynamic id parameter instead of the .helptext class

$(document).ready(function() {
    $(".helptext").each(function() {
        var helptext_id = $(this).attr("id").toString();

        $('#'+helptext_id).attr('rel', '../../AJAX/
GetHelpText.aspx').cluetip({
            showTitle: false,
            ajaxSettings: {
                type: "GET",
                data: "q=" + helptext_id
            }
        });
    });

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