There will always be a need for people to come together for larger projects than an individual can accomplish by himself. So some form of entity-level organization will be needed that can own stuff.
Let's say Sally, Jim, and Bob all work together to create a car washing service. They are successful and the enterprise grows. They decide to reinvest their profits and buy some bigger and better equipment. Does Sally get the power sprayer and Bob get the dryer? What about Jim? Are those things equal in value today? Will the be equal in value used? The simplest thing to do is to say that the business owns the equipment and Sally, Jim, and Bob own portions of the business.
Where I think the system went wrong was in limiting liability. All actions a corporation/cooperative/guild/whatever might take are done through the agency of a human being. At every step, those human beings are responsible for their actions. "I was just following orders" is not a valid excuse in committing harm against someone else on behalf of any entity. If Sally damages someone's car by accident, yes the assets of the company should be available for suit AND Sally should be on the hook personally. Maybe she would have been more careful.
I agree with you about liability. I've spoken for years about how we all should be living with full liability and no limited liability.
What I find interesting is that your discussion about the corporation uses an example of a mom & pop shop. Sally, Jim and Bob can sell the used equipment and split the proceeds as they feel fits their needs. No corporation is required. If Sally wants the power sprayer, she could pay for it with the proceeds from the sale.
However, your example left out some of the more insidious corporations like the state and the multi-national corporations that all interact and make demands of Sally, Jim and Bob. The three hard working individuals that you mentioned put all kinds of creative, work and energy into their little car wash business. However, the other corporations profit from that work through taxes, absentee ownership, etc. These entities became so large and powerful because they were allowed to survive the death of their owners and get passed onto their heirs. Call it a country, nation, kingdom, corporation, or what ever other word you choose, the IDEA that ownership can be stored within a dead body is repugnant and enslaves us all. It does not allow for the natural flow of energy throughout the planet and as a result we end up with uber rich and a lot of poor.
We need to support the Sally, Jim and Bob's of the world and they don't need a corporation to do it. They don't need to beg to a dead corpse for a corporation either. No support for those faceless, dead corpses! They need to be allowed to decompose to release the energy back into the environment for the living. We can organize ourselves without the use of dead bodies to do it.