You could certainly automate watering with a hose timer and a drip system. If you're going to put SH pots outside, consider the much higher UV levels and their effect upon your pots. Plastic and sunlight is generally not a good combination long term. Because I keep mine outside when temps permit, I use only ceramic and glass containers that I pick up at thrift stores, yard sales, etc and drill them myself for SH use. Glass can be touchy to drill, but most ceramics are pretty easy. In either case do the drilling under a trickle of water to keep the bit and material you're drilling cool.
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