Good grief, talk about thread drift, lol! How did we get so far from "how do I make it on 'x' $ a month and afford insurance, too"?
PcDreams, there's been a lot of good advice given in amongst the diatribes and accusations. I hope you are able to put some of it to use in your area and in VT when you get there. One thing I did when I was still in nursing school, many moons ago, really helped me survive without a full-time job, which I could not handle with school and kids. I would go to garage sales and look for good furniture (couches, dining room sets, etc) that needed cleaning, maybe some really easy repairs (resewing a seam, for instance). I'd buy them super cheap, bring them home (good thing you have a truck), give them a good scrubbing, do the mending (hand stitching works), and then place an ad in the local daily paper to sell them. For some reason, something someone would only spend $50 on at a garage sale, would bring $150 if advertised in the paper. If I only spent $25 on it, less than $5 on repairs and cleaning supplies (didn't have a steam cleaner starting out, bought one with the proceeds of the first few sales), and $5-10 on the ad, maybe $40 into it, sold for $150, that's $110 profit. A couple of those a month would pay for insurance for both of you through your wife's employment.
I also made a lot of money back then by buying garage sale baby equipment and cleaning it up, same thing - an ad in the paper brought buyers that were willing to spend more for clean, safe baby equipment. Think highchairs, modern cribs, swings, maybe carseats if they are current and haven't been in an accident. Maybe baby equipment doesn't do it for you, but I had 2 small boys back then, so I knew my market and did very well.
It helped that I lived in town back then, as you do. Folks could call me, run over and see what I had to offer in a short drive, and I only took cash, so the money was instant with every sale. Now that I live in the boonies, I only bother to buy queen-sized beds for resale. They are in demand, and folks are willing to travel to my out-of-the-way home to buy them.
Find your niche market, and work it.

If you like to make birdhouses, you can get the materials free at building sites, or pick up free pallets at businesses and use the wood from them for materials. There are lots of books on how to make birdhouses at the library - either for real birds or for decoration. Freecycle can be used to find free paint, old knobs etc for trim and decorations. I won a pair of birdhouses at the fair a couple years ago, and I use them as decoration inside my house. Nothing but rough cut boards, bundles of sticks and moss, and a couple old (or faked old-distressed) wooden knobs and a couple little handpainted signs with sayings like "Home Tweet Home". Very easy and simple, but cute. You don't have to have a ton of money into materials to get a home business started. You can sell your birdhouses at craft shows, on consignment at handcrafts stores, over the internet/ebay, farmer's markets, advertising in front of your (decorated with birdhouses, of course) house, lots of options.
Do you have a wood stove? If not, get one. I'm not saying spend a bunch of money on one. Through garage saling and Freecycle, Craig's List and similar sites, you can probably find a free or nearly free box stove - I even got a free Earthstove once. Same thing with the stovepipe and cap. Use those skills you are gaining in home repairs/improvements to install it. The same wood that you pick up for building birdhouses will burn just fine for heat. Do check your homeowner's policy (I'm assuming that if you have a house payment, you probably have a requirement to have homeowner's insurance), and make sure you jump through the hoops to have the stove installation certified so it doesn't void your insurance policy. That will save you a lot on heating for 6 months of the year and with a non-insulated home, that's important (can help your resale value, too).
Have you written down every penny that you spend for several months to see where the month goes (I have a feeling you have, but others in the same situation may not have done so yet)? This lets you see what unexpected expenses crop up to blow the budget, as well as what you can trim from the budget. Over time, keeping track of every penny also lets you see what recurring expenses need to be budgeted for in advance. For example, if you are paying the car insurance monthly, chances are that you are paying a fee each month for that privilege, either by paying that monthly fee or by not being able to take a "discount" for paying in full every 6 months. My insurance is 10% cheaper if I pay it every 6 months, in full, rather than monthly. If I don't budget for that twice-yearly expense, I spend more than I have to for car insurance. There again, selling one or two pieces of furniture, or using some other income stream to generate the extra money to put aside each month toward that expense, will meet the goal of saving 10% off the car insurance.
Want to cut the gas expense and stop driving your wife back and forth to work? Sell a few pieces of furniture or a lot of birdhouses, and make sure the cheap, high gas mileage car you buy with the proceeds is an automatic so your wife can drive it! That cuts your gas expense in half, and pays for that cheap car (lots of them out there for $500 or so) in a few months. Then put that money toward paying off your farm equipment or buying that insurance (health or auto). One small car for commuting, and your big pickup for hauling home lumber, garage sale buys, and cleaning out people's basements (and making you MONEY) should cover your needs. Even cheaper, if your wife's job is on the bus line and during hours the bus runs (not always an option, I know), is to have her ride the bus. A monthly bus pass is cheaper than gas/oil/insurance/tires/maintenance.
For more ways to stretch the dollars you have, and to avoid spending them

, check out the tightwad tips thread at Countryside Families. There are lots of good ideas posted there. Hope these ideas help you or others who are still reading after getting through the nasty posts.