Feeding outdoor tomatoes

If you sink some sort of tube - I use a bit of waterpipe or the top of a plastic bottle - into the compost when you plant up, you can water directly into the tube and it takes the water to the bottom of the pot and keeps it off the leaves.
Definitely stab some holes through the plastic liner, they need drainage - especially if they're out in the rain. I rarely water hanging baskets.

I did that for the one in the ground - buried the top half of a 2 litre coke bottle upside down next to the plant.

Not watering the hanging baskets is not an option here - my little south-facing garden gets very hot and dry in the summer, and the tomatoes wilt unless I keep a close eye on them. Of course right now it's a quagmire of sticky clay!