Why Does Everything I Touch Die?

Hello all!

Why are all of our Winter Butternut Squashes dying? We've had such bad luck with them this entire Summer and I'm just soooooo frustrated with it.

The first time we planted them, it was back in early June; we had a thing where we let kids from Orientation place Squash seeds inside Jiffy Pellets so that they can grow and we can transplant them later. Those died from over-watering. Squash seeds are prone to rotting before they even germinate and thus, why our seeds are covered by an anti-fungal powder. But the powder is no good when you have a disgusting amount of rain drenching the seeds. The very few that didn't rot (I accidently left those indoors, so they were protected from the rain) were quickly transplanted into their current position up on the hill. Here they are dying:

The Second time around, we tried planting the seeds directly to the ground. Of the 30+ or so of seeds we planted, precisely 2 actually germinated. We're not sure why the rest didn't germinate, I tend to think it's because I put them in too deep so they couldn't find their way to the surface and just rotted underground. However, my boss helped plant some seeds too and I know she's good at the whole depth thing, so that's most likely false. Essentially, we don't know why they died. Well, here they are dying:

Finally, we re-seeded everything on the second week of July with great success. Most all of the spots germinated - I was happy. Here they are doing wonderfully.

So, as you can plainly see, we have squashes that grew weeks apart. This is incredibly awkward when it comes to watering because I have some plants that want tons of water, while others don't necessarily need to be drenched. That's why, we think, the older plants are dying. Because they were so dry that they wilted down to a point where those leaves weren't going to bounce back to health. The older ones did recently go to flower, and some are actually making fruit:

But even those flowers are dying:

It could be that the flower wasn't pollinated, but I've seen so many pollinators in our garden, that I just can't believe that to be true. It could be too dry, but ever since we diagnosed the Squash problem, I've been wetting them like crazy. Maybe now they are too wet? I did actually cause some of our peppers to get root-rot from over-watering. I'm not sure anymore of anything anymore.

I normally don't like advertising all the bad that's going on in the Garden, but it's therapeutic. Fairfield loves reflection and the good it does. Maybe one day I will reflect on this issue and say: "wow, I put in so much work and they all ended up alive and well". OR, more likely, I will say: "wow, I put in so much work and they all shriveled up and died, mocking me for my efforts". Either way, I know this:

It's good to be a farmer.

~ jesusnunezx