So I've been wondering if you can do something similar to what Masanobu Fukuoka did with sowing two grain crops in one field that have different harvest dates, only with winter wheat and spring wheat. What are some other grain pairings would this work with?

On the note of Masanobu Fukuoka. Is the 'One Straw Revolution' book worth getting? I usually avoid buying books because I know I can't stop with just one. But if it's worth the splurge I'd love the excuse.

Most annuals are very resilient, so as long at they can grow in different seasons you could plant without clearing.
The only concerns would be that you have to use more seeds and that you will have to harvest before the new crop is over 3 inches.

So you could plant corn and then before harvest sow fava beans or kale or broccoli. There is really no special combo.

It is definitely a book worth reading, if not buying! More than a 'guide' for how to follow in his footsteps, it is also philosophical in the most pleasant sort of way.

Let us know how your experiments with this turn out!