Most seller's in a sub-to don't understand the risk they are taking and most lenders have concerns over the overall portfolio quality ratings which has an impact on their cost of funds.

If you are in the Tampa area and plan on purchasing there, I highly suggest you connect with @Josh Green.

I am in Florida and we have a strong STR market and most of my buyers bought at high rates and using AirDNA we were pretty spot on for the numbers and we were successful in being profitable.  

We pay $850 for a WH install, so, that seems high but you are in CA.

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

I know a lot of Chicago investors are here too; but if you were in my spot would you recommend Chicago as prices are too high and I have never been to the city moving next year.

Seems like a high-risk, low reward situation though.

Funny story is my ex wife's mother went to grammar and high school with OJ.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

I am seeing high 6s at 75 LTV with a 720+ score.