Over watering in open containers should not occur as long as adequate drainage is provided. You can always drill a hole on the side of the container about 1" to 1 1/2 inch up from the bottom so in case the bottom drain holes get blocked or you put a saucer underneath the container it will still drain.
I have used 5 gal buckets and did not put holes in the bottom but a couple on the side as described above and never had any drainage problems plus it provides a small reservoir at the bottom from which the plant can draw water from kind of like an SWT (Self Watering Container).
Ami
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