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always line my baskets with plastic compost bags and add moisture absorbing gel and granular plant food. you could try putting a plant pot saucer in the bottom of the basket before you put the compost in or try using a loam based compost
Put a shredded disposable nappy in each one.
The most recent one I've done, I've set up with two timers, one for the sunny front, one for the more sheltered rear. Like you I do two waterings (with the front getting a third mid-afternoon dampening on manual if the landlord remembers in hot weather). I use a spray, adjusted to the basket size, to ensure full coverage.
Timers being unintelligent things, I try to encourage the customer to use a (small amount) of discretion in heavy rain. Having said that, the front baskets, being exposed and under eaves, pretty much need watering even after a deluge.
I also force myself to go around to the pubs and check on the baskets, offer some advice, every so often. I spent twenty minutes the other day showing the customer how to dead head. Sadly it was the end of the day so had to have a pint too!