It's hard to predict the future, isn't it?! I've roamed the U.S. in a small camper and a van (on vacations) for many years. I lived in my van (a little old Ford cargo-type) for a straight stretch of seven months when I didn't have much else. With a large dog, a cat and a litter box.
The most important thing is what is best for YOU. I think you've got that down quite well. It's easy enough to ignore strangers, but it's less so to ignore the people who are close to you (emotionally and physically). Most of them are giving emotional advice to you on something they know nothing about, and it usually won't apply to you. Other people are also quite free with advice on what you should do with your valuable belongings (like real property), with much of it not being in your best interests.
Most of the van campers and boondockers seem to fall into one of two general categories: 1) Sell everything and go, and 2) those who have a place to go home to if things get bad. The first tend to have limited means, and the second have property, a good retirement or healthy bank account.
One thing I've noticed since I've been checking out this subject (several weeks) is how many of the first type are often quick to advise you to downsize to virtually nothing, and they insinuate that you are a 'failure' to boondocking (etc) if you own anything that you can't fit in your van. I literally cringe at this. You're not going to sell your things for anywhere near their value, or what it would cost to replace them if you needed to.
Someone suggested that you stay on your own property in your vehicle, and rent out the house. This could be a step closer to helping you make a decision, plus having other benefits. The privacy fence and a garden are good ideas, but it also allows you to keep a close watch on what the renters are doing with your property. Talk to landlords and listen closely to the horror stories: extreme damage, cleaning up after horders, meth maggots, people with 'anger management issues' who take much of it out on the house with an axe, those who pay and then stop, and you have to have them legally evicted (often difficult if they have minor children*). Now think of living a thousand miles away and you didn't know it was going on.
Suggestion: If you have a home that is larger than you need, choose two rooms if you can, and dedicate one to KEEP and one to GET RID OF. Gradually go through your things and box them up (Home Depot has pretty cheap boxes for $1 to 2 -- having just two or three sizes makes them easy to stack), and set each in one of the two rooms. Not only does this help fix in your mind the level of importance of each item, it will help you decide what size storage unit to rent.
I am sort of looking at becoming a boondocker, due to my low income, the deterioration of my house, and my frustration at being unable to maintain this weedy, rocky acre of poor soil.
Personally, I'm not getting rid of my extremely comfortable queen bed, or my books, and some other things. I'm a DIY person -- mainly due to circumstance -- and getting rid of all my tools and materials literally scares me to death.
Your #1 Priority: Do What Is Best for YOU.
*If you can't unload bad, non-paying tenants, talk to a lawyer. We have a tremendously bad meth problem here in WA that the county doesn't want to deal with, and Child Protective Services that doesn't do its job. Some landlords were having a hard time evicting them because of the kids, until one of them discovered that if they were to put the house up FOR SALE, the sheriff would evict the deadbeats. So, several of the landlords put their properties up for sale and just traded them to each other. It was legal. It was just about the only smart thing I've seen here.
