As a young man thirty years ago, I too shared your aspirations, but after five years of truck farming five acres, the bloom came off the rose. Growing the stuff was the easy part. Getting it picked and selling it at a fair price was the hard part. As another poster said; Pick-Ur-Own is the way to go but only if you live near where your customers live.
Small farms can be financially sussessful if they can produce a niche crop. If there are resturants nearby, find out what fresh herbs they use and grow them. Big bucks on a little as an acre.
I, too had a Farmall Cub. Great machine for cultivating but I wouldn't plow or disk with it. The engine's too small. Hire someone with the proper sized equipment or buy something bigger to do your ground preparation.
Finally, if your real goal is the ag tax exemption. consider leasing your land to a local farmer and continue to garden for your own pleasure.