>> I've done that with huge pots, but with smaller pots, I just find it easier to hand water so I can check which plants need water or other needs.
That makes a lot of sense. I was thinking of the drip-timer-pot idea for growing cherry tomatoes in 5 gallon pots. With a not-very-water-retentive potting mix, I might need to water them 2-3 times per day at the peak.