Nice to have you on GN. Enjoying all your posts, especially this one. So you have already started living your dream, cause you are making a plan. The power of writing down your dreams increases the motivation to achieve them. Your dream reminds me of a Canna Cribs episode on Artisanal Grown husband and wife team just south of Portland, Oregon.
Personally I threw my career away just over 10 years ago to start subsistence farming on a small homestead in South Africa. It was an abandoned drug rehabilitation centre before I got here. My background was IT, with a little farming experience. When I first came down I started rehabilitating the farm, getting infrastructure in place such as sewage, electrical, water etc in place. The first thing I actually did was create a vegetable garden and then I moved onto building a private wifi network as there was no access to internet.
A couple months ago I came to realization how far we have come while I sat drinking my own beer, smoking homegrown tobacco and cannabis, eating spinach, eggs and bacon from the homestead. It was living my dream.
My partner and me are about to take another giant leap and I recently ( last week ) purchased ( made a deal with another farmer ) a lister 3kVA engine and generator. This will technically mean we can almost be off-the-grid and be self-sufficient, except for diesel.
About your crash learning, dont worry too much, you are about to embark on a life of learning something new everyday. A suggestion would be to stick to your trade, strengths and look at multiple revenue streams to keep things going. My biggest battle when coming down was thinking I could do it all myself and manage an IT business remotely. I lost my business while I was hacking away at farming and that made life very difficult. 10 years later we have separate revenues like renting out a cottage, wifi subscriptions, selling eggs, pork and vegetables.
A couple things I wish I had done differently. Although I have setup a small orchard, I wish wish wish I had planted more fruit trees 10 years ago. I wish I had setup a proper orchard with irrigation and security fencing.
And to make your life easier and more rewarding, get a good dog. This was the start of my journey, traveling around to find a good spot to live the dream and then finally moving down.
From homegrown to full blown commercial. That was a pie in the sky dream for me. I am happy where we are, and never going the route of legally licensed cannabis. Luckily its legal where I am to grow several plants, and I am fairly happy with that freedom.