Do one task at a time in each app so you can compare apples to apples.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.

It seems from your post his desire (problem) is he wants to get out of owning and managing residential real estate, and your desire (solution to his problem) is you are interested in taking on the task of owning and possibly managing a residential rental, so you just have to make the deal work for you both and if it doesn't work or his demand doesn't work with the numbers you've ran already than don't be afraid to walk away.

However, it is harder to scale SFH, buying 4 at a time is no easy task.  

However I am searching for a real estate investor in the La Crosse, WI region or Rochester, MN (willing to commute) that is looking to hire a dedicated helper or assistant if you will for help with whatever task, big or small!

Just like in any task in life, starting without any plans will likely end in unexpected/unplanned results, very likely failure. 

I posted about my first ADU project in San Jose back in 2019 and shared 3D visual, pictures and numbers if you are interested: https://www.biggerpockets.com/...Building an ADU could be a daunting task and takes a lot of $$ and effort.

Is there a middle ground where I can have someone do the bookings, price changing, administrative tasks, and they get paid a salary or percentage but I still end up not paying PM levels?

An example of this is inspections (with photos that are uploaded to your owner portal), your properties financials always available online, and any tasks being accomplished for the property visible to the owner.

How can I start looking, and what would be the process for this task?

Do one task at a time in each app so you can compare apples to apples.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.