I'm right with you. My dad was a farmer and taught me: First deal with the irregular, annoying parts on the outside. Create rectangles with a long side and turning space on each shorter side. Then deal with each rectangle by going back and forth along the long edge. The turnarounds are also a great place for some wheelbarrows to collect the clippings closest to the Komposthaufen.
Hence why I went for the irregular strange part on the lower left first, and then the more regular part on the right. That's the weird rain collection, herb garden, thing we have at the back.
> Then deal with each rectangle by going back and forth along the long edge.
I prefer to work in lands after I have cut the headlands. Reduces turning stress on the grass and acknowledges that the machine (the one I own, but the design is common) is optimized for use in one direction.