I, personally, focus on midwest markets, specifically Detroit and Memphis with 7 doors across those cities.

My suggestion would be to come out to as many in person meets as possible (https://www.biggerpockets.com/forums/521/topics/1177645-tax-...), ask tons of questions, and figure out how to hang out with people who are doing what you want to do (add value, work for free, do anything to get that experience.What area of Chicago are you looking to invest in?

It all comes down to where you balance your personal perception of risks to the potential reward.But, in hindsight, I sort of align with Melanie.  

However, after the exchange, they want to transfer from personal name to an LLC under their Holding Company to protect their assets. 

I was told that indpendence is a high crime drug area (this was by someone who lives in the overland park area - friend of a friend - not a real estate person).

They provide no real protection at all for the borrower/contractor relationship.So, if your house had some plumbing work that was done, and your contractor did not pull permits and they did not have the city inspect the work, then when you go to sell the house you will get caught and they will tell you that they need to open the walls to inspect the plumbing and then closing the walls and repainting are on you.The draw process is way too easy, I've learned that it is sooooo worth paying your personal inspector like $100 to do a deep inspection. 

Quote from @Greg Williams: I've been using a software called BatchLeads for about 6 months now and that is what has been a game changer for me personally.

Building relationships in person can be invaluable.

My recommendation would be speaking with a local agent/property manager who has personal experience with investing in San Diego real estate and can complete a property analysis for you to determine current value, highest and best-use, and what your options are.

There's no right or wrong answer because it all depends on your personal goals.