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Rubbermaid Tubs

If you use these things, which I personally think require a lot less work and a lot less water, you need to punch a hole about 2 inches from the bottom and make the hole large enough to stick a water outlet in. The best are the same ones they use for boats (around me they're cheap - $2.99) and they don't leak at all. What I do is have 5 of these tubs in a row and plastic tubing off each one. I have a master tube that goes to the drain and this keeps the plants from getting waterlogged as well as providing some air input into the water.
I do not have holes in my tubs. They are 20 gallon tubs filled with top soil only. I considered punching holes in them near the bottom as has been suggested, but instead I just carefully monitor the amount of moisture in the top several inches of dirt. I also monitor the plants that are growing in them. In the last month and a half I have found the plants wilted once and watered them that day (about a week ago). I had not watered them before that except when I transplanted them into the tubs. These tubs are in my greenhouse dome and the humidity level is quite high in there. Last week (when I watered them) it was getting up to 100 degrees in there during the day and that's probably why they wilted, but the soil was a little dry in the top two inches, so I watered them anyway. They are perky and growing like weeds now.