Tomatoes are probably a wash ROI-wise, except if you grow it yourself at least you know what has (or hasn't been) sprayed on it. Most of the flavor has been bred out of production tomatoes in favor of uniform growth, maturation time and ability to withstand the rigors of shipping. There is a drastic taste difference between heirloom tomatoes and store bought.

I've got a several EarthBoxes that I put my tomatoes, peppers & eggplants in and those require vitually no maintenance and you just fill the water reservoir and they essentially water themselves (fill them once a week). My brother successfully grew pumpkins and cucumbers in EarthBoxes with trellises for them to grow on in his driveway so I'm going to experiment with squashes this year. I've always just thrown wood chips or composted leaves between the rows which drastically cuts down on the weeding.

A lot of people make gardening a lot more difficult than it needs to be.

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1980 300TD-China Blue/Blue MBTex-2nd Owner, 107K (Alt Blau) OBK #15
'06 Chevy Tahoe Z71 (for the wife & 4 kids, current mule) '03 Honda Odyssey (son #1's ride, reluctantly) '99 GMC Suburban (255K+ miles, semi-retired mule) 21' SeaRay Seville (summer escape pod)