
James C. answered 04/10/20
Computer Science Instructor | Here to Help with All Things Web!
Unfortunately, this is one of those cases where it is probably best to reconsider the requirement or go forward with what feels like a hack IMHO.
This is a tough requirement because positioning the item will take it out of the flow of the document and, therefore, kills the wrapping. Floating, like you said, makes it hard to position.
I have seen people accomplish this programmatically (JavaScript) and have even seen some CSS hacks that involve CSS3 transforms work. So, I guess it can be done, but neither of these are an ideal solution and each undoubtedly presents drawbacks.
The one thing I have learned about technology over the years is that what most people think is simple is really hard and the things people think are impossible are often times rather simple.
That's just my two cents. All the best!