I believe it’s important to address these two items separately: First, there  are still ways to find out the identify of the member(s) behind the LLC and secondly these anonymity strategies do not actually shield liability because claims are still brought regardless of whether the members of the LLC are identifiable.

I have a few things I am hoping to get some guidance on if possible:1) Can itemized deductions just be the quotes for things needing fixed/ cleaned?

We know no more about him than you have told us, but just the list of items you mention give me pause - "He's been trying to get into real estate for 6 1/2 years."  

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

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

I will definitely not renew the lease, the lease renewal is in March.

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

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.

When the leases were up, I didn't renew and put non-section 8 tenants in.

The current tenants have a lease until end of January, which I will honor.