This tomato bucket idea sounds very similar to the Topsy Turvey tomato planter that is advertised on tv. If you go to the web site you can see how it works and this idea sounds similar only would be much cheaper. While you are describing drilling various holes on the sides (similar to a strawberry jar planter) I think you could just drill one hole in the bottom and stick the roots in the hole so they are inside the bucket then fill w/soil. The holes in the lid would allow for watering. I think the variety of tomato plants you are referring to comes from a company called Bonnie Plants. The website is www.bonnieplants.com. I bought some of their tomato plants at my local farm store today. Hope my two-cents worth is helpful! :)