Hi Eric,
New York City, eh? Had you considered the South? A great deal of difference will be made in your choice of what state you pick.
I am assuming you are considering doing this solo?
You mentioned western Massachusetts as one of your possible locations. I have something in common with you in that I grew up in western Massachusetts and at age 26 I tried to homestead there, 40 miles from my parents' house. Why it didn't work, had everything to do with the regulatory environment and the lack of practical information that was pervasive in those days. Before the internet, if the public libraries didn't have it, or if you didn't know it was there, and someone in your circle didn't know it, it was almost certain you'd not run across the information any time soon. I purchased 8 acres on a dirt road up in the Berkshires without much to start with, and after 9 months the
local town muni-guys shut me down because I hadn't jumped through the right hoops. I got out while I was ahead, and sold it off at a
profit since I had at least had it "perc" tested. Doing at least a FEW things right, as a clueless kid, paid off handsomely. Lesson learned. Open yourself up to the possibilities where people aren't breathing down your neck. That was the end of my New England chapter.
Number one consideration is the regulatory environment. A state where you can do what you want with your land without guys with official seals on the side doors of their trucks coming up your driveway messing with you. The United States is great because it's a supra-national federation of independent countries. Crossing state lines changes more than you might realize.
Kentucky and Tennessee are right up there as foremost recommendations firsthand. I am in the process of building on homesteads in each of those two states. There are PLENTY of counties in Tennessee, including the eastern part, where you can do what you want to with your land, no restrictions. Meaning, you can live how you want to. Set it up as a campsite, build your home out of whatever you want to use.
Your advantage of having a long growing season and a mild winter will greatly enhance your chances for success. You don't want a place where the only access five months per year is by snowmobile, followed by a two-month "mud season." The less you have to be focused on fueling your furnace, or
rocket mass heater, or whatever you use for heat, the more
energy out of a day you can focus on getting the important thnigs done. Your health will be greatly impacted by your routine in regards to exercise, the chores you perform on a daily basis and how you live in concert with your environment. Living off-grid is ideal, but that's easier said than done. Generate your power using a diesel or
gasoline generator and somehow locate close enough to cell towers to have your phone serve as a Wi-Fi spot. It's key to be able to do a
project the way you want to do it, WHEN you want to do it. Not be dictated to by the weather and your road conditions, topography, flooding, etc.. It's much better to have chosen your homestead in a place where it snows just once per winter, and your
chickens, your goats, your whatever you're raising, don't have occasion to cost you extra just to pull through the winter. Appalachia extends all the way down to past Birmingham, and lots of it is a lot more sparsely settled than up north. We have hiking trails, lakes, fishing, boating, scenic views, all of that.
Come here first, even if it's just for a day or two, and learn everything you can about your topics. Bring a blank notebook and take copious notes. Talk to real estate agents, and the people that work in Rural King, Lowe's, Tractor Supply.
Let's just suppose you follow this
thread of suggestions and come down South and get your 4-plus acres on the "one-payment method." Craigslist is just one source of potential sellers. Search the web using Startpage dot com. That way, you're not looking at the world through Google's biased agendas, what Google chooses to show you. LOOK FOR COUNTIES THAT DO NOT HAVE A "BUILDING INSPECTOR." They STILL EXIST. Go a few miles out of town. Ask a local real estate agent to ONLY e-mail you information on pieces of land in such-and-such a county(ies) with asking price at or below the figure you specify. What time of year you do this has a lot to do with what prices you'll be offered. The spring rush in March isn't an ideal time to buy. But it's an ideal time to start work on what you already bought. Work, get your 16-inch mini-chainsaw, learn how to start it ,and use it safely (start with cutting up stuff that's already felled before you do the Paul Bunyan thing), and get something in the ground that's both livable for an overnight camp, and secure/lockable/behind barbed wire, have a dog(s) for security, etc, before the hot, humid weather sets in about the second week of June at latitude 36 North. Come prepared with some kind of vehicle that can serve as a camper. A mini-van, at a minimum. Ideally, a camper that is towable as a trailer or a power unit camper that can be both lived in and driven. Get conversant with living the truck driver lifestyle. Sleeper cabs don't have running water in them, but they always park near where they can walk to a restroom at 3:00 AM. I tore the rear seats out of a pick-up truck. Best modification I ever did to it!! Truck stops, 24-hour gas stations, large shopping centers afford safe, convenient overnight parking where no one messes with you these days. Used to be, you'd wake up to bright flashlights and thumpings after an hour and a half, but that was 2005. The cops have a lot more to worry about these days with all those 10 million extra economic illegals streaming across our southern border with free bus and plane tickets to wherever they want to go. Just keep your wits about you, choose your overnight parking spots judiciously, lock all your doors and keep your windows tightly rolled up (cars and trucks are built purposely with PLENTY of ventilation by default, in places we never suspect, including the vents in your dash - - you DON't run out of oxygen, keep 3 extra keys on you at all times, plenty of drinking water and sanitary supplies, diet supplements (I take fifteen (15)), and 4 or 5 black sheets and towels with bungee cords for privacy curtains. You can sleep down to minus 4 degrees F outside air temperature comfortably with five (5) polyester fiberfill comforters if you're dressed warmly. A knit hat is an essential, since 50% of your body heat is lost through your head and neck areas. Having extras helps in the winter months when finding things takes up non-negligible blocks of time with the sun above the horizon only 9 hours out of every 24.
Survival skills in transition, will be key to making a homestead work on a shoestring. Did I mention personal financial management skills? This is not for the undisciplined or the faint of heart. Knowing what your lifestyle is costing you "on the road" eliminates all fear while you're between income sources. And yes, Tennessee and Kentucky do have plenty of colleges and universities where an academic can find a position. But keep an open mind. There are all knids of
income streams available for someone witjh teaching skills. Personal fitness trainer, freelance tutoring for kids, home health aide come to mind.
If you bring a spouse/partner and/or family members with you, it is essential that they be on board. A team of people can get so much more done. But there has to be unity and a singleness of purpose. Learn from Scrum. Meet every morning for fifteen minutes and remove obstacles out of each other's way. Every day is a glorious adventure.
I hope this helps.