I tried that upside down tomato growing and the only problem I had was it got so heavy esp when the tomato was full of fruit that it started pulling out of the planter. I had to take string and wrap it around the planter from the bottom up over the top to keep the plant from falling out the bottom.
For now, I will just grow my tomatoes in my tire planters. The cherry tomatoes I put in hanging baskets and let them hang over the edges.
My tomato sprouts are just loving the morning sun in the kitchen window.
Marti