Here's a little then-now:
Shockingly, I haven't killed anything, hooray! The tomato plants are growing fast and tall and were starting to crowd the other planters, so I took a couple of them and decided to give the upside-down technique a try. Instead of buying one of those ugly cylindrical things you see on TV, I opted to make one myself out of a simple hanging planter.
I cut a 2" hole in the fiber liner and gently pushed the roots up through the hole. Using a scrap of tough cloth (a reusable grocery bag in this case) I cut a smaller hole with a slit about the diameter of the stem and wrapped that around the stem on the inside of the planter, letting it rest on the floor to prevent soil from pouring out.
With the help of Boyfriend (he held the heavy thing to keep from crushing the tomato) I filled the rest of the planter with soil and added some oregano, rosemary and nasturtium at the top. Hopefully the tomato plant will survive. I'm already not expecting a great yield since my plants never see direct sunlight, so at the very least it will give us a smidge more privacy from the neighbors across the way.
Speaking of nasturtium, this plant is taking over my entire balcony! The only way this thing could be more resilient was if it were made of plastic. My poor phormium and dracaena are practically being evicted from their home.
I've propogated the nasturtium out to other planters, which is as simple as pinching a clump and shoving it into some dirt. And to think, I was SO excited when those first two orange flowers appeared, now I'm throwing away clumps of the thing every day!