Hi,
The convertion of numbers to click to call only works for static content.. any content that is dynamically done or modified (via javascript), won't get converted. Perhaps you are noticing that, a refresh is done via ajax and an element in the page updated with the ajax call, that will make numbers not to be parsed by the extension.
Maybe what you notice with the menu has something to do with some javascript refresh of the page content? The only way to tell would be to write a totally static web page and load that, and check the click2call numbers and context menu entries, then refresh that 'static' page and check again. My guess is that you are opening some kind of application that updates content via javascript and thus numbers are not reparsed for click 2 call and somehow affects the action submenu.
As for opening two popups, there is no plan to do that, bu you could write a "glue/proxy" page/script that could open those two popups, and then open that glue page instead of the regular want you want. That proxy page could open up the ticket page, another page, updated a database and do whatever you like as you are free to write it in any way you like.
Best regards,