Planning to upgrade our MOLTO installation

Since I am thinking how to integrate our MOLTO tools to our website, I am considering upgrading the underlying CMS to the latest version. This is always a scary and tricky move so I need to carefully consider all the options. FYI the documentation on the upgrade is http://drupal.org/documentation/upgrade/6/7 and in case you have an opinion or a comments, please let me know. I'd love to hear what you might be thinking about taking such risks.