For what it is worth (maybe nothing --grin), some folks take a very long time to begin to mature. Asking a Jerry to come up to speed in half a year, or even five years, often is like trying to get a batch of wine to mature overnight. Can't happen.
The more opportunities the Jerry's in this world have blown off in the past, the further behind the 8 ball they are and the more entrenched in their non-productive habits.
It is understandable that you'd want to find a permaculture way to handle such folks, hopefully swimming WITH the flow, and not against it. However, some of these people change very, very slowly (think: like watching grass grow) and in the meantime, they can bring your organization very nearly to its knees (one bad apple...). Jerry's cause a lot of stress on others around them. It's stressful to watch someone else suffer. Yet if you jump in, you end up enabling their refusal to learn and grow.
Your operation there is like a big net, and when you haul it in, you have a little of everything in it: some stuff has to be thrown back and other stuff is "a keeper." So someone has to be the "Chief Sorter and Tosser." They have to be able to handle the unfair/untrue accusations hurled at them by taking control of the situation and not firing back.
Example: When I worked at an inner city high school, there were many parents and students who would expend considerable time arguing, but very little time doing much of anything productive. These folks had learned to argue until they found an edge, then work that edge for all it was worth. And us staff knew not to give them an edge to 'sharpen their sword on.' So when we said something which was a decision or a statement, and the other person gave us a long full-blown argument, we did not address their arguments. That would be pointless (as I suspect you've discovered with your "Jerry's")---one must simply digs in one's toes and repeats your statement...You stand your ground and repeat the simple statement you started with and frequently, that's all you say. It sends a statement that this is the way it is and you are NOT going to be change. It's sort of similar to dogs and horses. The one who steps aside is the lesser in the pecking order. You do not step aside but you do not attack either
Often, explaining, elaborating, embroidering, illustrating...all are utterly pointless because this is NOT an intelligent discussion--it's simply arguments for the sake of the Jerry getting to continue his poor choices.
It's generally worked for him often enough to endear him to that method, but chances are, not often enough to secure him as cozy a niche as he feels he deserves. Chances are that he has bombed out of jobs, worn out his parents and friends or girlfriend, and to their relief, he's flapped off to your place.
Paul, you simply cannot be everything to everybody! I'm sure your dear companion has made that observation a time or two as well. As an inventor, innovator, facilitator, procurer, teacher....you need the monkey taken off of your back with regard to such social management issues. You have, I assume, already formulated some sort of expectations regarding the assistance people are to render in exchange for being there and learning. Fair enough. Perhaps now it's time to search out someone with experience in dealing with a variety of people (perhaps a retired teacher). And then, it's time to practice the fine art of delegation and trust. No one always makes the perfect decision, 100% of the time, but a seasoned veteran of people and issues will come doggone close.
Best wishes, Cheri, Reedsport, OR