It does look great, and is very common in California in everything from tract homes to multi-million dollar customs, but I assume Illinois is not as big on stucco. 

Also, can you customize his excel files or are they password protected?

I assume you would need a specialized attorney to help navigate the waters of purchasing.

It was all about what his customers wanted, not what he wanted.

This varies a lot depending on local custom and the type of property. 

There is free landlord software out there that allows you to customize your online applications and ask for documentation (proof of income/proof of employment etc).

I have tenants who are not Chase customers and can still use Chase Quickpay to send money.I've also considered asking for post dated checks from tenants.  

Then I jumped in my vehicle and drove home...hoping it wouldn't ring again, since it was 8:45 PM now and I was sleepy.Upon getting to my home office, I logged into my cloud based CRM (Customer Relationship Management) program and documented everything that transpired, including what was said in the initial call.  

Multiple showings at your convenience, I stopped doing things at customer convenience a long time ago.

I have a Google Voice number set up with a custom recording, I don't see how anyone would know the difference.