He preceeded to tell me he just got done with a wholesaling course and that the instructor (who licensed a well known real estate investor whom does not even deal with residential properties) told him that he can routinely obtain houses in a short sale platform where he can make tons of money by offering properties to wholesalers at 50 cents on the dollar.

Airbnb's fate has been challenged and steps are being taken to cripple or disable that route, but long term, you will have a great home or great multi family rental.

We work with the local Alderman and Police to make sure our properties are routinely checked on.  

Do they handle coordinating routine vendor services such as pest control/pool cleaning, or is the owner required to coordinate that?

Tenants with lousy rental histories do tend to focus on dealing only with private landlords because they know larger company do routine screenings while we "little" guys might not.Gail

So do you think I should just keep the property, add the sump pump, and routinely waterproof the walls every few years?

I now recommend having them sign a contract saying they will communicate status once a month with distributions (even if status hasnt changed) and hiring a company with an internal maintenance person so as to avoid paying excessive maintenance fees for routine things.

If you don't know what direction to go you'll never get there.4) Develop a routine.  

Hoping to get a reputable property management company to manage the property while providing me with routine updates.

Everyone keeps saying read this, read that, can someone just feel it in their heart to show a disabled person how to start off?