Along with the important set of questions outlined above around what your own needs, desires, and skills include, also ask some questions around what the
land's needs, "desires" and skills include.... Every landscape has an intrinsic agenda, usually involving a succession of
native and perhaps exotic plants proceeding over many years towards a steady state, infrequently punctuated by restarts. A particular suite of animals, insects, fungi, etc. accompany the plants. Try to find out what this is, both by research and by observation of nearby sites in various stages of succession. Much of agriculture involves frustrating this process, often involving annual tillage or other forms of major disturbances. Weeds, sometimes including brambles, tree seedlings, etc. keep trying to move the system further along. You will make your work easier by considering how you might work with this process rather than against it. The general trend of
permaculture thinking towards reliance on a diversity of
perennial, often woody plants as opposed to annuals is a guideline following from this.
Thus, assuming you are in a climate that in its wild state supports some kind of forest (30 inches of rain a year in zone 5 reminds me of where I grew up in MI; even though you dont give your location), what kinds of useful
trees could you incorporate into the system? You probably have wild trees trying to come up anyway.....