I've been slow to update this thread even though I've been regularly taking pictures and continuing my taste tests.
I usually pick tomatoes twice a week, and usually get a 1-2 pot fulls every time. More than enough for my family. Here's a picture from Sept 10th of all of the tomatoes that had accumulated. Even now, I usually have about 2-3 pots always full of tomatoes. Now that it is getting colder, the number of tomatoes is decreasing so I expect to wrap things up by mid to end of October at the latest.
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