Looking for solution to have specific terms have automatic tooltips whenever entered into content items
You could write custom javascript that wraps all strings you want to replace with the &lt;span data-toogle="tooltip"&gt;&lt;/span&gt;

here's a tutorial

// Pretending we have more than one paragraph to look through
jQuery('p').each(function(){
    traverseChildNodes(this);
});

function traverseChildNodes(node) {

    var next;

    if (node.nodeType === 1) {

        // (Element node)

        if (node = node.firstChild) {
            do {
                // Recursively call traverseChildNodes
                // on each child node
                next = node.nextSibling;
                traverseChildNodes(node);
            } while(node = next);
        }

    } else if (node.nodeType === 3) {

        // (Text node)

        if (/CMS/.test(node.data)) {
            // Do something interesting here
            alert('FOUND A MATCH!');
        }

    }

}