Way too many people have unrealistic ideas when it comes to homesteading, it's not a 5 day week 9-5 job, homesteading is like ranching and farming, it takes absolute dedication. Many things can be bartered but cold hard cash is still going to be needed and a means to replenish it. I know several homesteaders that started young but continued to work and some that started in at middle age but purchased much of what they needed years before, today one works a part time job and the other works full time homesteading until they do retire.
If one chooses to have a well, pay yourselves the water bill. We put $100 a month away for well repair, filtration and re-drilling, in the well coffer we keep $12,000 (it took a few years to build this up) available using as much rain water as in keeping as few hours as possible off the pumps. If one are lucky you can also find static wells thus all you would need is a pitcher pump. Years ago I had a state hydrologist come out on the property and marked on my USGS map the best locations for drilling, the service was free not just in this state but many others though not sure if they still are today?
