Before your feature request is addressed, an alternative approach
could be to use a page action instead of (or in parallel to) the
context menu. Page actions are designed to alert the user and offer
actions that apply in a limited number of pages under certain
conditions.
You'd need a content script detecting when the page meets your
criteria (and you have full flexibility to check whatever you want
here), in case then you trigger a page action with a popup offering a
button (or similar) to execute the action you currently assign to the
context menu.
This approach would also have the advantage that the user would be
alerted (by the page action icon in the omnibar) when that specific
action is available instead of having to know beforehand when it's
available and right click to get the context menu.
Just an idea.