1. with a contractor you are creating a contract around the deliverables and the time frame for those deliverables. You do not have the ability to reach into the contractor and have any say in how the work gets done (e.g. can Bob work on this task Tuesday instead of Thursday even though it's not related to interfacing with me). To me this satisfies the "person is free from the control and direction of the hiring entity in connection with the performance of the work" part.
2. "the person performs work that is outside the usual course of the hiring entity’s business" is the tricky one, but I think it more has to do of what you explain your business to be. If you are running a SaaS platform and enter into a contract with someone who provides software development expertise the relationship between your business and the contractor is different. In the cleaner case in one of the other trajectories there is a difference between someone providing supplemental cleaning services for existing cleaning businesses and someone who provides cleaning services. The relation is probably distinct enough to be interpreted this way, as someone pursuing to sell their capacity to someone else is different than a business acquiring a contractor to deliver the goals of their business.
In the Uber case a driver who works for Uber to deliver their core business is different than a company formed to provide taxi service capacity to other companies who are running a taxi service.
3. Then the last clause "the person is customarily engaged in an independently established trade, occupation or business" I think for software development this is easy to say when someone is trying to demonstrate themselves as a contractor vs. someone who is 'hired' as a contractor.
I think if you are worried about really the first case that is just something that should enter your contract language as a deliverable of the other entity. The relation between you and the entity you are contracting is different than discussions with the downstream contractors. Since the smaller contractors inevitably have this end up being the same person this could be confusing. Based on the writing of this rule I feel like you would be able to ask the entity for updates, information related to the deliverables, schedule meetings, and so on. You may be able to ask for accurate accounting for hours worked but you can't have any say when those hours were because the entity would be billing you the number of hours.
For the second case I think you would be fine if you were soliciting someone to contract some hours to work for you because the other person would be representing themselves as a consultant who has hours to sell. You would be buying hours of work in expertise X which is different than your goal of selling Y. If the relationships were built this way then I think this satisfies the third clause as well as because then this contractor would be in an independent business who could satisfy the terms of a contract between entities.
I feel like as long as you treat the other party as a business and not a person, and the other party understands this you are able to operate normally. You may have to emphasize this nature more to be compliant with this rule and focus on milestones and deliverables and contractual obligations (it is still fair to say to enter a contract that says it has to be delivered by 2pm Friday), but you have to keep your hands off defining hours to be available/hours on call/punch in and punch out times, etc. I would stick with buying and selling hours of work for some contractual outcome.