NewGardener95 said:@RpR currently I have planted squash cucumbers & tomatoes. So essentially, after I have dug the hole, I should water every time it dries up?
And do you recommend all of the above, such as coffee grounds, as a replacement for fertilizer that I could buy from the local garden center, such as gypsum?
No the hole will tell where you water level is and how well the soil drains.
The items I listed are for working into your natural soil to improve it but if it is a slough, you will have to raise it so the roots are never in the puddle zone.
If it holds water and never drains, you are going to raise the entire area or use raised beds that are well off of the ground.
For what you grow , squash and cucumbers simply need the roots to not end up in water so there a small, in area raised bed would be fine, you could put down straw to keep the fruit out of the water when it puddles but tomatoes, depending on how many you plant need to be well out of the ;puddle zone and the trunks need support .