Some homesteaders have gotten their lives
simplified to the point where they barely buy anything from the
store. We're in a sort of halfway house --- we do buy flour,
cocoa, sugar, dairy, tea, and some meat; keep two cars running; and pay
for high speed internet and electricity. On the other hand, we're
extremelly minimal in most respects and can live well on the poverty
line income for two people. If you're obsessed with clothes,
sports cars, or all of the latest electronic gadgets, you're obviously
going to have to make a lot more money.
We could easily make more money, but we figure that the time we spend
working for more money isn't worth what we'd buy with the extra
money. We'd rather chop wood ourselves than spend those hours at
our computers, give 30% to Uncle Sam, then pay someone else to do it
for us. Sure, we're probably only getting minimum wage for our
wood chopping, but we're getting a lot of satisfaction too.
So, my short answer is --- you can do it if you're willing to live
minimally! Web development and remote management sound very in
sync with homesteading since you don't have to drive anywhere to do
them. And having enough money saved up to take the first year off
work makes it seem much more feasible.
I can't imagine life on the farm without Mark. On the other hand,
I'm pretty attached and can't imagine life anywhere without him ---
obviously I survived just fine on my own before he came along.
In a way, going solo has a lot to recommend
it. Since I have Mark (and the pets) to keep me company, I have
very little reason to get to the know the neighbors, and I'm ashamed to
say that I only know a few of them well. It sounds like you'd
have a lot more incentive to build a community, which will really help
when you start freelancing.
Once again, it all comes down to time. Mark spends about 80% of
his working day doing farm chores --- cutting wood in the winter or
working in the garden in the summer, checking on the chickens, or
building up our infrastructure. I spend maybe 20-40% of my day on
farm chores. Of course, we're also in the middle of lots of long
term projects which you might not have to do --- burying our water
line, building a root cellar, etc.
As my mom would say, where there's a will there's a way. If you
really want to live on the land, you'll be able to make it
happen. I'll look forward to hearing more about your homesteading
project!