First off, so you don't immediately jump to expectations of culture shock, I grew up in fairly rural San Diego. We didn't get electricity until I was four years old, and that took my father having connections to someone in the corporate office of San Diego Gas & Electric in order to get poles and wire run several miles to feed one house. Also took about $20K of my folks' early 1970s cash. We had no neighbors. Raised cattle.
I now have a family. Three young sons. Oldest just turned five. Youngest is six months. My wife was raised in the suburbs but has a pretty good idea of how I grew up and understands the value of that as it applies to raising boys. She is not gung-ho about moving away from civilization, but she is willing to go for it.
We are watching the direction of our current state of residence and it is pretty clear that the values are going as far away from ours as possible. We are conservative christians. Bitter clingers if you will. There is another thread on this forum in which someone from Chicago has some complaints about KY. Most of their complaints fall in the positive column for us. I think that we would fit in ideologically.
Who we are:
I am a self-employed licensed general contractor. Or is that self-unemployed?

My bride worked as a corporate financial analyst until we made her a stay-at-home mom. I am not under any illusions about improving our income by moving to Kentucky. Construction is in the tank everywhere. I am currently working as a handyman. We are living on about $25K/yr. We are able to do this with a serious focus on priorities. We don't need an entertainment lifestyle. Don't need the latest greatest widget. We grow some of our food (one reason for moving to KY is that it looks like we should be able to afford room to grow more of our own food). I am able to take care of all our home and vehicle maintenance. We only spend money on the basics.
If we cash out of CA (i.e. sell our home) we will probably have something between $250-300K. It appears that can buy a decent sized farm in KY outright. An alternative might be to not sell, but rather rent our house in CA, but I am not sure that anyone would lend to us at this point. We have excellent credit, but the income side of the equation should be questioned. Odds are we will have to sell in order to move. Buying something outright in the $200-250K range would probably be most prudent so as to have a bit in the bank to handle surprise expenses and to give a bit of time to try to find work.
We would like to keep commutes within the 30 minute range for most things. If it takes a bit more than an hour to get to a larger town/city once every few weeks that is fine.
With regard to education for the kids, we are homeschooling K-6 for sure. Junior high is up for debate. Ideally we would like to send the kids to a public high school. Kentucky gets good grades on homeschooling. That is one of the reasons we are looking to move to KY.
I would like to be in an area where the kids can learn to hunt and shoot outside their own back door, and if anyone hears it they won't think twice about the gunfire.
We would like to find a church in which to be involved. Baptist? Mennonite? Something where the Bible is preached and lived.
One thing which we are interested in, and which I suspect will be difficult to find, is reasonable access to a martial arts studio. My three year old is one aggressive varmint and I want him to learn that there is a discipline to fighting and that it is NOT primarily a form of recreation. I think a martial art will provide him with the appropriate outlet for his aggression and teach him proper use of it. For the sake of the rest of the world this is a factor for us to consider. I think if we find ourselves within 30 minutes of a martial arts studio we will be within range of any other services we would be likely to need.
We would like to live somewhere with at least DSL internet service, but that is not an absolute must. It would also be nice if it were a place where UPS/FedEx would deliver (where I grew up they wouldn't).
I am looking for a place with an absolute minimum of five acres and ideally more than fifty acres. I definitely want there to be water on the property. Be it a spring or a stream, I want year around water which I can access without electricity. I want enough cleared space to have a large enough vegetable garden to be able to feed hungry boys, plus space for cattle and some feed for them. I also want trees. I want them as cover for game and I want them for raw material as a woodworker (one more reason why KY looks good to me--If I move there I intend to purchase a portable bandsaw mill). I would like to have more species of tree than just poplar. The more walnut the better. Cherry and hickory are good too.
Lastly: Pie. Blackberry to be precise. With vanilla ice cream on top. But I'll take a big slice of hummingbird cake on the side with it too if it's available.
First question: How much of a negative stigma do we bring with us by being from California? I know that in some places Californians are not exactly welcome. We seem to get branded as Kalifornicators. I can't say the stereotype has not been earned, but we aren't all hybrid driving, tree hugging metrosexuals with purse dogs. Will rural Kentuckians welcome us, or will we be looking at decades, if not generations of "outsider" status?
Second question: Does anyone have pictures of the "mountains" around Berea? I have heard mention of them in the picture thread, but I didn't register seeing any of them. It may be a function of my personal standard for mountains. Some of the eastern KY pictures had some nice little mountains. I would be happiest living in relative proximity to such geography, but my bride is not so keen on eastern KY. I may have to forgo my mountains, but if I can have them and keep my wife happy then we all win.
Third question: How much work could a person expect to find working as a handyman? In other words, how self-sufficient is the average kentuckian?
Fourth question: How much work could a person expect to find offering services as a sawyer? How common are lumbermills?
Fifth question: Particularly for those who have also lived in warmer climates--just how cold am I likely to find Kentucky? I have one friend who swears he was colder in Tennessee than he was in Kodiak Alaska. He blames it on the humidity. Is it really that cold? For those who may know, how deep is the frostline in your particular area?
Apologies for the long query. I hope I have provided adequate context for my questions.