So their plan is follow Hawaii’s “protect the homeowners plan:  how did that work out?

My girlfiend and I are looking in La Grange and Brookfield which is not quite as fast west as you, but my aunt lives in Wheaton so I am quite familiar with your area.What's your game plan over the next two years? 

The tenant refused to communicate about his plans to vacate and finally left the key under the mat on June 2 but made no communication, so we had to make 4 trips looking for the key.

Use LVP flooring, it's cheaper than installing new hard wood floors and they're more durable for longevity purposes.

In this manual (which I assume could be modified to provide to tenants) I include all the financing information (which you would not include for tenants) bank accounts, mortgage accounts, payment information, and mortgage payoff), a list of the contractors, what each contractor does, a list of upcoming planned or necessary repairs, and a copy of all leases associated with the property.

Unless you negotiate a new contract or addendum with your PMC, they do NOT have to abide by any requests/demands you make that contradict what's written in the management contract.If they have in fact NOT followed the terms of their contract, then you'll want to send them something in writing pointing out the specific language in their contract that they violated and ask what they plan to do about it.If they fail to correct or address the issues, then you'll want to start looking for a new PMC.

At a minimum,  you should understand what the current zoning is and what restrictions there are.As the post above mentioned reaching out or going in person to speak with the planning and zoning department will be very helpful. 

If I were you keeping the property as 4 units and renting out bonus unit under the radar may be your best option especially if you plan to refi or do HELOC while occupying. 

My plan would be to use the equity loan from the second home to purchase another great deal (3rd home) and use the rental income from the second home to pay towards the equity loan and then start renting out the third home to get rental income and start paying off the mortgage on the 3rd home.

If tenants say they want new flooring, then we have to put in new flooring, even if damage was tenant caused.