LucasB95. Kinda took a big bite, eh? I've put my thoughts about the overall situation down below, but I think you're at more of a "farming" level than my "gardening" experience covers, at least when it comes to creating vegetable beds of that size, so I'm going to put out a call to a member who is a farmer and who might be able to steer you in the right direction.
@Porkpal? I see you have a farming badge. I wonder if this is something you can weigh in on, or point Lucas to some resources?
My thoughts: You've already recognized many of your mistakes, so that's a good start. Besides what you've already identified about over-watering, my immediate thought is that the underlying clay soil might not be draining well and you need to load in as much compost and manure as you can, plant a cover crop and leave it alone until next spring. The 60' strip along the barn is barely getting enough direct sun for tomatoes. What direction does it face? It might do well for different crops. A lot depends on your climate. Where are you?
Find a food pantry that can use all those pounds of kitchen seasoning. They're not going to do much for your garden. Get your soil tested and add amendments based on any deficiencies that are indicated. Your local agricultural extension service should be able to help you.
Part of your problems with chewing pests is that the environment is off-kilter. While you're waiting for your beds to settle in, plant native pollinator plants all around the area, as many as you can. If they're natives, they'll still need watering for the first season, but you shouldn't have to amend the soil. Once you attract a thriving population of beneficials, the bad guys will diminish in numbers. Also, intersperse your crops--big groups of the same plant attract big groups of the bugs that eat them.
Another approach would be to forego tilling and go with a more permaculture approach. Have you ever researched hugelkultur? It seems radically different, but it is an alternative to "fighting" the soil. Creating healthy soil takes awhile; ideally, you start on the soil the year before planting.
I don't know what to advise about your current crops. Photos would help, knowing what pests you have would help. It's hard to combat fungus once it takes hold.
