@Ethan Slater here's some info we hope you find useful:Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

If it is unclear as to whether you have met the standards of the Illinois Code, it is recommended you speak with an attorney for an explanation of Landlord/Tenant Law.

We segregated them from any degree of competition, failure or necessity to conform to any standard.

I do relatively well in my day job by today's standards but my hourly rate for self managing is closer to that of a surgeon. 

When clients come onboard, that process should be explained in great detail and by signing the PMA, you are agreeing with our standard processes and core values.Far too often that process is never fully explained and/or proper expectations are not set, hence new clients try to tell you how to run your business.

In fact assuming attached 4 small standard San Diego units, my maintenance/cap ex would be $1200 or almost 12% in your scenario.  

I've found the easiest solution is to have a really strong banking relationship and then they will be able to provide non-standard offerings. 

That seems like an expensive roof - does it need to be completely torn up and rebuilt to hurricane standards?

This requires an income that allows you to maintain your standard of living throughout your life.

And a drain within reach of the standard drain hose?