Squash does best if you can transplant it when pretty young. I like to plant it out before it gets more than 2-3 sets of leaves.

Harvest earlier and see if that helps. If not, plant a different variety next time.

Squash plants prefer warm weather and typically live for a few months. They don’t like extremely hot weather or when it gets cold. Both of those will kill the plant.

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There are two types of blossoms, male and female. Pollen from the male needs to be transferred to the female blossom (by pollinators or by hand) the female blossoms are what turn into squash. If there are no females present you can pick the males at any time. If there are females present you can pick the males and hand pollinate the female when both flowers are open. If you want to eat the male blossoms they are best tasting when still in bud form.

Squash vine borer. Here’s an article with tips that may help: https://growinginthegarden.com/organic-pest-control-that-really-works/

I would harvest by size, not by color. Summer squash is best when harvested young.

This could be a couple of things. Pollination – if the fruits aren’t getting pollinated they wither and die. Prevent this by hand pollinating when the female flower is fully open. The other issue could be the heat. Depending on where you live, in hot places like the low desert of Arizona during the hottest months of the year, the heat destroys the pollen pretty quickly and the plants are done producing. Normally at this point, I pull the plants and then plant again with the monsoon moisture in the middle of August. By the time those fruits ripen, temperatures will have fallen back down.