There is a new Atlassian feature in beta called goals which might be the thing you are looking for. We are piloting that feature right now.
Another solution would be to have a dedicated page for each milestone and use the combination of page property and page property report where the milestone page contains a page property table with fields like name of the milestone, date of the milestone and status (on track or not).
Finally, another option is to have a specific Jira project for the milestones where you can maintain the status tracking at that specific Jira issue.
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