Urban matrix problem

Dear people,

I am trying to solve a problem shown  on the picture attached.

I have an outline of an plot and within I try to create a generative urban solution. The idea is to create a matrix with blocks consisted of same geometrical characteristics and intersect it with boundary geometry (in this case the beggining of the existing street profile) By rotating the matrix from -90 to 90 Degrees I try to test which of geometry intersections will generate the biggest surface area and to pick the best one. At this point I recieve problems like in a case attached. For some angles for e.g. 0, 25, 45 (example riht) I get clean urban solutions with nice cutout courtyards but in some cases like in this rectangular outline version, i get mistakes where for relatively simple geometry the offset function fails. I have tried so far with reconecting curve exploding and joining all over again, even fliping curves and offseting in positive direction but some systematical solution which functions for every angle I didn't manage to find. in all cases i manage to find an angle which produce such mistake....and since it is a part of bigger gh script where it is not purpose to interfere within the search process and should function without problems automatically it blocks me in further development.

In case some of you have idea how to resolve this "simple" problem I would be thankfull for your help. gh file is also uploaded...

Many thanks in advance!

Best,

Aleksandar