I think the raised bed garden is the way to go for the tomatoes this year. The soil drains better and you get less weed pressure compared to planting directly in the ground. I built mine last spring using untreated cedar boards and they have held up beautifully through the rain and the heat. I would suggest putting a layer of cardboard down first to smother any grass, then add a mix of compost and topsoil. The plants have been producing well into October with that setup. As for the watering, I set up a simple drip system on a timer so I do not have to remember to do it every day. It uses way less water than a sprinkler and keeps the leaves dry which helps prevent mold. I can send you the exact parts list if you want to put one together. The cherry tomatoes have been especially productive this season and the raised bed makes harvesting so much easier on the back.
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The pasta sauce I made last weekend turned out really well so I wanted to share the approach. I started by slowly cooking diced onions and minced garlic in olive oil until they became translucent, then added crushed tomatoes from a can and let it simmer for about an hour. The trick is to add a small pinch of baking soda to cut the acidity, then balance it with a little sugar and dried basil. I also threw in a parmesan rind while it cooked which added a nice depth of flavor. You can freeze it in portions for later use and it reheats really well. I served it over homemade pappardelle which I cut wide so the sauce would cling to each noodle. The whole meal came together in less than two hours and everyone asked for seconds. I used canned San Marzano tomatoes this time and the difference in sweetness was noticeable compared to standard canned tomatoes.