Answer: Your containers should be drilled with approximately 5 holes, 1/4-1/2". Put 4 holes in a circular arrangement and one in the middle. Add a layer of coarse gravel about 1/2" thick to the bottom of each container. I would recommend a homemade soil blend (my recipe to follow). Such soil is free of disease, weed seeds, holds moisture well, retains plant nutrients, and is lightweight and portable. My recipe is as follows: one bushel each of vermiculite and shredded peat moss, 1 and 1/4 cup of ground dolomitic limestone, one cup of 20% superphosphate, and one cup of a complete fertilizer such as 5-10-5. All material should be mixed thoroughly, adding a little water if overly dry. If I'm feeling sassy, I throw in 2-3 handfuls of composted cow manure. Your tomatoes can be sidedressed with the same 5-10-5 when the first fruits appear, and then 3 wks. after that. Follow package instructions. I have obtained the best results from 5 gal. containers when I place only one plant per bucket (even if they are very small plants). Remember, containerized plants are more susceptible to drying out so give them the equivalent of 1" of rain every week. Use lukewarm water if possible. A thin layer (approx. 2") of mulch will help retain soil moisture. You could use shredded bark, straw, grass clippings, nut shells, newspaper, etc.
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