Morning @Kyle Trotta I believe the city is a great location for investors of all experience levels and strategies.

Minut multi sensor (but mainly for sound levels for us), zwave everything (door contacts, yale locks, thermostats, water leak sensors, temp/humidity sensors, garage door controllers, garage door tilt sensors (to see if the door is open/closed), security cameras covering all exterior entrances plus the driveway, zwave lights switches to remote control lights on exterior security floods and/or certain lights inside the property, some type of doorbell cam, zwave motion sensors, Samsung Smartthings hub, wifi smart plugs for certain devices inside...and the list goes on. 

Until recently, they were collecting rents in person, but they are no longer able to, due to advancing age and disability.Does anyone out there please have some candidate property management companies, that are reputable and honest, and would be willing to service this level/number of apartments?

I’d keep it simple and say that nobody really knows if and when the next crash will happen, especially looking at the local level.

Simple answer is they just base it on per square feet and construction quality level.

And finally, with regard to your concern to banks caring about your education level.....they don't.

To get your business going I would suggest Miracle Morning for Real Estate Agents followed by 7L: The Seven Levels of Communication and then The One Thing.

My strategy is to use base level finishes whole leasing it and replace with upgraded finishes once I'm ready to sell it in 7-10 years.

It took me years and hundrets of deals to get to the level where I am.

I personally don't pay an extreme amount of attention to marco trends (yet) because I am not investing on a macro level yet.I am more focused on the trends of the area I am investing in (Chicago in my case) and like you, for my first handful of deals I prefer to be close to them.