It will make your tenant happy (or less pissed), it will give you a fall guy if things don't go perfect and it frees up your time to go find more deals and make more money.I quit doing anything to my units unless they are empty and I just feel like going over and painting or whatever.I am at the point I just want to manage and collect checks.

Going deeper, there is a ton of data backing the fact that the SF real estate market performs quite strong, historically speaking.The 2008 crash was quite abnormal in is scale, and was greater than any other downtown going back to the Great Depression. 

I charge a flat fee to market the property, screen applications, get the tenant under contract, and collect the first/last/deposit.

First, I still had to use separate spreadsheets to track particular data points because Buildium didn't have the data fields I needed.

My lender pulled a FICO 4 from FDC factulal data corp.

Essentially you are asking the seller to report on the actual rent collected and expenses for each of the previous 12 months on the building. 

They also mentioned it could be subjective upon the individual auditor, and in their experience the auditors lean towards the side of collecting for the IRS.

I thought I will collect it later along with the deposit.

I am going to use hard money lenders and will be collecting capital funds from 2 family members. 

This website provides useful data on shootings in Chicago neighborhoods, https://heyjackass.com/.