So I believe I finally know what has been affecting my tomatoes. Maybe this coming season, I can finally control it.
See link below for more info. Lots of info on Google as well. Source: Anthracnose on tomatoes
P.S. The featured image “Mr. Tomatohead”, is not showing the results of Anthracnose. Catfacing is caused by something else and I’ll update when I remember what it is. It was chosen for the featured image simply because it’s an imperfect tomato (but don’t tell Mr. Tomatohead that).