We currently own and manage one rental property and the tenant pays us via Venmo and we use excel to track expenses. As we scale our portfolio, we want to make sure we have good systems in place for accounting, tenant...

I didn't know that Illinois or Chicago had a similar law, but other say there is such a requirement.From a practical standpoint I wouldn't state electronic payment through Zillow as my only payment method in a lease. 

DISCLAIMER: NOT A LAWYER or anyone practicing law on this planet or another within the solar system.However I would think if something happened it would take a competent lawyer about 30 seconds to say "The mortgage is under @Peter Hoang so the veil should be broken and we can go after his assets as well". 

Check in with lenders to learn more about the practical aspects of doing this.

Builder level except I am going to put in window sills, as a practical durability feature.5. 

Nobody on the internet can give you the perfect answer without being properly trained and licensed in the specialty, being in the practice for years, and knowing your whole situation and your personal goals.  

Here are the guidelines utilized by the IRS practice unit when they are conducting an audit of Section 179D studies.How does a company/taxpayer go about claiming this deduction?

Typical appraisal practice does not include verifying permits.

If a property manager like @Drew Sygit is seeing highly questionable business practices in their market, he is going to call it out, but his viewpoint is in regards to his market.  

I tell them to practice, 1 hour later everyone is kicking them out just as good.