Bruteforce types just itterate over all the possibility down to a certain resolution/accuracy.
One way would be to extract the overal skeleton midline and have a centrpoint travle along it, calculate circel interceptpoints and if there are 4 intercepts, calculate the area.
Another way would create a grid to a certain resolution and look for largest amount of griblocks covering the area whilst being a square as a total.
Finding the exact amximum on a arbitrary polygon however is a tad more complex.
Type in your question and check out the possibilities posed. Better polish up your math though...;)
There are a lot of papers you can download on this issue.
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