Congrats on your growing garden! I'm glad you and Baby Bunny are enjoying the process! I have a friend that uses upside-down planters every year to grow tomatoes and/or peppers. She also puts plants in hay bales and the ground. She gets good yields of both with the planter but I think she only plants cherry tomatoes in it.
The only advice I'd give you is that in the heat of the summer she has to water the planters at least twice a day. Stuff that's in the ground/hay bales isn't as needy water-wise. Oh, and deer love to nibble the tomatoes in those planters since they are at just the right height!
