Hi @gore. Many thanks for your questions, I'd be happy to give some advice.
For caterpillars, my go-to suggestion is always Yates 40g Natures Way Caterpillar Killer Dipel Insecticide for edible crops. It is a certified organic caterpillar controller with no with-holding period, which means you don't have to wait to eat crops after applying it. I've had fantastic feedback from everyone I have ever mentioned it to.
The winged insect I am not sure of what it is exactly. Let me mention @Noelle one of our very knowledgable members on horticulture to see if she could offer some advice.
You've got me! Hard to identify the flying insect from the photo - I really haven't a clue. If it is seen sucking sap or chewing your plants then @MitchellMc's recommendation of the Dipel insecticide will be effective. It's a great product that isn't harmful to the plant, environment or you and controls chewing and sucking pests very effectively. If this insect isn't causing any harm, then let it be. It has a place in the insect world somewhere.