Single post in Tip Fix Maybe?
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[tip] can be a powerful tool, but as you've seen it does have its limits. Contents of a post cannot ever be allowed to overflow beyond it.
Any attempt to automatically calculate whether to tooltip is inside or outside the content area will inevitably mess around with the many templates and codes that users have on their profiles and shops, among other things, causing far more problems than it would solve.
Not to mention, [a tooltip can contain variable content] so calculations would have to be dynamic and complex. Overall, just not realistic.
If a tooltip's contents cannot be read, then it is a legibility issue and the responsibility of the post creator to notice and fix - we do have a Preview button, after all.
Like an Accordion
See?