And I noticed that many of the unfurnished units were offered with a month to month lease... the kids would get cheap furniture that they didn't care about tearing up and giving away when they were done.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases.

Leasing agent, maintenance guy, property manager, city hall-economic development, building permits. 

-I will then put in place a lease agreement between ourselves personally to the new property management LLC to lease the cottage and between the ownership entity of the other rental property to the prop management company. 

You need to hire a Commercial agent to lease that for you.

Ideally he will be stay there for 10 months and lease the property from the new owner while he gets ready for his move. 

However, one of them said they won't move in for 5 months but will sign the lease now, even though they're still renting another place during that time. 

Do you have any clauses in the lease about cleanliness that they are breaking? 

You’re not reliant on others to weigh in on special assessments, leasing regulations etc.

In short it doesn't matter if you increase how much income a residential home is leased out for that will never improve your property value it's always based on how much homes in that area sell for. commercial real estate on the other hand has a few other ways properties are valued including the income approach.