I know it still looks pretty bad, but I assure you it's a HUGE improvement over the neglected bushy mess it was before. I took care of most weeds, pruned the tomato plants, straightened out the ones that were crooked to hell and gave them new supports. Took me probably like 3 hours

Wow! Job well done!

There is a point in every tomato season where I just can't keep up anymore and I need to convince myself to do these larger clean ups.

For me, it's when it gets too out of control that I end up with crop ruining issues like slugs (if I don't keep the ground clear, trim off bottom branches) or mildew (if I don't maintain airflow).