When you have found a general area where you want to settle, visit there first.
A small vacation, maybe a camping trip.
But don't keep to yourself!
Talk to locals. Talk, not interrogate! Find a popular local spot, I do NOT suggest a bar, a coffee shop would be a better choice! Mention to someone that you are planning on moving to the area. Once you have said that, they will give their opinion on the area, the people there, etc.
Get a copy of the local paper and check out the classifieds. What jobs are available in the area? Read the paper...see what local governments are doing. Are they encouraging growth? Are they actively trying to bring new businesses into the area? Walk around and check out what businesses seem to be thriving...and which ones aren't.
It would be nice if you could move to the country and not have to worry about money, but, alas, most of us have to work. Unless you have a home based business already established, you will have to get a job in the locality you move to.
Especially if you are moving to a very small town, finding a job can be difficult. No big box stores or franchise fast food joints. There are mainly local businesses, run by folks that were born and raised in the area. It can be hard to get your foot in the door.
When you move to your chosen area, expect to be without employment anywhere from 1 to 6 months.....until the local folks get to know you. Make friends with your neighbors, they can be the best way to get information about local job openings.
You may find yourself in a job you never expected to do! Go with it. Every job is an opportunity to learn something new.
If you do plan on having a home based business, check to make sure you won't be stepping on someone elses toes! If you plan on selling, say, baked goods out of your home to local farmers markets and such, check to see if anyone else is doing the same in the local area. Competition is good, too much competition hurts everyone!
I was woefully unprepared when I moved here. I was extraordinarily lucky that the Darlin' Man was able to get a job as quickly as he did. Even so, we are struggling. For the first time in my life, I had to apply for fuel assistance. I was never able to find a pellet stove that fit in our budget and was in decent shape. Even with the fuel assistance, we will have to apply a great deal of his check towards heat for the rest of the winter.