On my 82 acres, there isn't much land that has NEVER been worked, but some of it lays fallow for decades before being cultivated again and gets very soddy with goldenrods and barnyardgrass, so that's what I'll talk about.
On this sort of land, I would use one of my farm tractors to plow it under first, choosing depending on the size of the plot needed. I have plots ranging from 1/4 ac. to 1 ac. right now with a combined tilled area of approximately 3 ac. I have 5 tractors to choose from from 20-60+ HP, and a 1-bottom plow, a couple 2 bottom plows, as well as a couple 3 bottoms. I would usually use my Case DC-3 as a preferred plow tractor, with a the 3-bottom plow behind it. It isn't necessary to have this many tractors or plows. 1 will do, it will just take longer if it is a smaller machine for a larger piece of land.
By a 'Craftsman', I assume you mean a lawn tractor... I think a lawn tractor would have a serious problem with having enough weight to dig very deep or pull very much soil. With tractors, the engine horsepower doesn't mean a lot if it doesn't have the weight to do the work. Soil work is hard stuff and can quickly bog down a tractor. Most lawnmower/lawn tractor weights are in the hundreds of pounds range. As a comparison, my Case weighs over 5,000 pounds (and we have wheel weights on it besides that make it even more). Even my lightest tractor, my Allis Chalmers B, is 2,000+, and with that tractor I would be fine to use the 1-bottom plow only. I think anything a great deal less would have a very hard time busting the sod as you have said.
Anyway, once I have plowed it under, it is left to dry for a few days if very wet. Then, I take my set of 3-point hitch discs to it, usually behind my International 656 as that is my fastest tractor (though the others are fine too). The purpose here is to chop the soil up after the plow turned it over. Going a bit fast chops it up better; going too slowly just furrows or slices it. The waiting-for-it-to-be-dry is important too, otherwise if the soil you plowed is still wet, the discs will just slice it into muddy clumps rather than chopping it. It is fine to re-disc a 2nd time too after another drying period if the first period did not accomplish desired fineness.
You can also rake dirt clumps off of land or crush them better by using a 3-pt. hitch landscaping rake or soil pulverizer, though I don't even own these and never have found them necessary.
If you are still having trouble, and are just looking to plant a small plot, 1/4 ac. or so, a rototiller may be what you need, not a tractor. A rototiller is capable of 'plowing under' as well as chopping up the soil in one swoop and on fairly small plots it is all you really need. 1/4 ac. would take a little while to do, but not terribly long - definitely wouldn't be anything close to a full day of work or anything. I find that it usually handles sod just fine, but if it is still too clumpy for you, you can use a handheld bow rake to rake some of the 'stuff' out of it. Don't worry about getting it too fine though, and some stones are okay.
It is also possible to work the soil completely by hand with handheld implements, though this is a great deal of work and I know I wouldn't want to do it on anything larger than a flowerbed.
Barring anything else, you could hire it done. Usually after the first initial breaking-up, the soil is much easier to work in following years as long as it is kept worked and isn't allowed to lay fallow for a long time to get grown into sod. After it is broken the first time, you may be more successful with the lawn tractor later.
As far as planting, usually on small plots I just cast or hand-seed the grain seeds and then rake them over lightly with a bow rake. I have done this with barley, oats, wheat, and flax and they seem to grow fine.
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