(I live about 2 hours away from the property over in southwest Florida myself). 

Any recommendations for title companies in South West Florida around the Tampa area? 

I know every market is different and I am in southwest Florida (which is a crazy busy market right now), but I just want to pick your brain and see what your thought process was. 

For example, suppose you plan to buy residential properties on the southwest side of the city.

You, or someone you hire, will also have to put a lot of time into this, which of course directly or indirectly increases your cost.What LinkedIn tries to discourage (through limiting messaging, capping contacts, and even suspending your account) is contacting and attempting to create contacts with everyone who fits a general criteria - like commercial mortgage brokers licensed in Texas, or  apartment operators owning real estate in the southwest.  

My interest is in buying rentals (single family homes, condos) in southwest Florida (Naples, Estero, Bonita Springs).

Currently own a primary residence but looking to connect with someone to expand my knowledge and discuss more about investing in my first rental property in the Chicago Southwest suburbs.

There's a lot of 2-4 units in Berwyn, Cicero, Forest Park, Melrose Park, and a few other surrounding west/southwest suburbs (Aurora, Elgin, etc).

Currently own a primary residence but looking to connect with someone to expand my knowledge and discuss more about investing in my first rental property in the Chicago Southwest suburbs.

I would like to meet with people who can share specifics about their experiences with short term rentals in the area.I am also open to meet with others in the southwest Florida area.