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Best way to connect and seal two plastic water containers?

I'm launching a little balcony gardening project that involves water reservoirs. I don't have much experience with these kinds of projects, so I need a little help.

Due to some dimensional constraints, I will need two regular plastic containers (your typical storage containers), and I was hoping to get away with only including a way to fill one of them. That means I will need to connect it to the other in some way. So I thought I would just drill a hole in both of them and stick a pipe between them.

  1. What is the best way to drill holes in plastic without risking any splitting?
  2. How do I make sure that the holes are water sealed afterwards? Can I glue around the pipe and plastic box?
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