Hi Domidii! Thanks for your critique. :) I'm happy to say that after drawing ~60 boxes in the 250 box challenge, I have finally been able to start doing what you suggested:

utilizing previously drawn lines to parallelize with, visualizing that orientation and doing the previous advice to plot the following points.

Sometimes it takes awhile for things like this to "click" with my brain, and I was having such a hard time visualizing the orientation, but I wanted to let you know that this advice has been really helpful as I work towards completing the 250 box challenge. Thanks again!