>> If it requires too much watering/care when I move to Florida I will replace herbs with succulents.
Have you ever experimented with wicks? If the herb planter stood up on something above a pan of water, some compartments could have two wicks dropping down into the pan, and other compartments could have one wick, or smaller wicks, or bigger.
Then just fill the pan as needed or tuck unneeded wicks up out of the water.
A dangling wick also protects a very young or small plant in a water-retentive pot from over-watering from the top. Excess water will be pulled out of the pot by the wick and drip on your deck, or evaporate. Sometimes I set seedling trays up on a chair or bench on a cotton flannel mat, and let that dangle, or a strip of fabric dangle, so it can drip and evaporate to remove perched water from the shallow seedling cells.
The 'dangle" is an important part, because it lets capillary attraction PLUS gravity pull the water down and away. If gravity didn't make the water drip away, the mat would just become as saturated as the bottom layer of soil and stay that way while the roots drowned.
