I don't know about the borers, other than they will probably be visiting my squash soon, first time I planted squash.
As to the watering, when I gardened in extreme southeastern La., I would water every few days, deeply. Make note of when it rained and how much, a rain gauge is invaluable. I would write it on the calendar, becoz you will forget.
Plants sometimes wilt a little, or even a lot, in the afternoon heat, this does not always indicate a need for water, as they will perk up in the morning. Raised beds are good for the drainage too.

Ditto what Louisianagal said. Better to water deeply a couple times a week (barring rain) rather than a little every day.

Can't help with the squash ... borers were always a problem when I grew them. Now I just buy at the farmers' market instead, lol.