Thales, congratulations! I'm jumping in too late to give you advice, but I was reading through your thread intending to write and urge you to take the plunge. I was delighted to see that you'd done it!
I was a dyed-in-the-wool urban pioneer - grew up in the ghetto and never even had the sense to dream about living in the country until I met my husband, who obviously knows me better than I do. To make a very long story short(er), I took the leap - at 42. We took a job as caretakers of a log cabin, off the grid on 70-some acres of wilderness. Nothing like maintaining your own infrastructure to teach you the ropes! We now own a few acres of our own, and we're s-l-o-w-l-y building ourselves a place to live, as we can scrape the money and materials together.
I have never been happier, and although we have had some very hard times, I have never for a minute regretted my decision to leave a stable job I liked and had worked for 23 years. I finally decided that if 42 years hadn't been enough to fully appreciate city life, I was probably doing it wrong.
At this point, I feel a LOT more secure with my retirement money sunk into land, driveway, septic, and well - all paid for, thank you very much. We're right on the edge of too old to start this, especially with no money to hire help. I don't care. It's the adventure of a lifetime, and I'll never regret it.
You've gotten a ton of great advice, most of which I heartily second. Sure you'll be in over your heads. If you were carrying a credit card balance, or crippling school loans, or even a car lease, I'd be advising patience. But it as long as you're not starting out with an appalling debt burden, it sounds as if you've got the determination and the smarts to figure it out as so many before you have. Some of them are even on this board to help you out.
And what would you rather have if what you're dreading actually happens - the knowledge that you played by the rules and are now watching your hard-earned savings dwindle away, or a few acres of your own land under your feet to fight for?
Man, I can SO relate to your need to get in there and start clearing! Here's our story - so far - which I'm sure will be extremely entertaining to everyone who's got more sense than to try and clear a driveway on an unbuildable lot, at 55, with a chainsaw and a musician's budget...
http://uppertupper.blogspot.com/