When you move to new territory, even if it is the same macro-climate, it may have much different micro-climates that what you are used to. I'm very familiar with the climate of Southern California, but gardening in Ventura county is different from gardening in Orange county, which is different from gardening in northern Baja. You need to be observant and flexible enough to notice minor differences in temperature and precipitation, and figure out if you are in a relatively dry place having a wet year, or vice versa. Farming occurs on the large scale and requires the farmer to play the averages -- average planting date, average rainfall, average temperature, etc.; gardening, which is more what permaculture is about, occurs on the small scale, where you try to adjust and adapt through the growing season. If it's unusually dry, you irrigate and mulch more; if it's unusually wet, you work on swales and drainage.
Often when the word "homestead" is used, it implies a radical change in the new environment: Mormons leaving Illinois to homestead in the high, arid plains of Utah; people raised in Brooklyn moving to a Kibbutz in Israel. When you don't have a few years experience with the climate, it makes settling down and growing your own food that much harder. Even when you do have the experience of a few years with the weather, you may not have directly observed the effects it has on the crops you want to grow. If all you have done is raise corn and soybeans, you won't be prepared for what to expect if you have to switch to sorghum and okra.
This is my 13th year living near the Fall Line in the southeastern U.S. and I am still learning new things, trying new plants, looking for the right variety for this combination of weather, pests, and weeds. If I were to pack up and homestead someplace else, the further away from here I got, the more difficult it would be.