My property managers are all incorporated so its my understanding that no 1099 misc needs to be issued by me to them for their monthly retained fee, they in turn do issue 1099s to all unincorporated independent contractors that perform work on my properties.So even though I do claim 199A QBI benefits for all my Rental Real Estate activities (as they satisfy the 162 trade or business standard), I assume there is still no requirement that I file a 1099 Misc as I make no payments to unincorporated independent contractors?

Chicago is EXTREMELY neighborhood and block specific, so the data can skew quite easily. 

(tuition, rent, and stuff like that are all covered by either scholarship or my parents helping pay for it, which I am extremely grateful for).

The great thing about SLO is that the vacancy rate is extremely low, typically about 2-3% due to the college.

But I'd take their numbers with extreme caution. 

In the end if there was a problem that persists I would then look into an area rug from somewhere extremely cheap, or a used piece of carpet.

If your market isn't extremely overpriced compared to some of the OOS markets you are looking at then I would consider starting out in your backyard. 

The current landlord and his wife (who was the agent in this transaction) were extremely nice and very helpful.

You can do something like just see what the difference in ROI is between a house that brings in the 1% rule and a house that brings in the 2% rule and once you do it over and over, you will start to know immediately what price to pay for the amount of rent that a house will produce because you will start to understand and find your comfort level of how hard you want your money to work (If you are comfortable with your money working extremely hard and producing what may seem like a higher return, "sometimes" you will invest in lower class areas because the price points are low compared to the rents). 

I'm sorry that my questions was extremely vauge and didn't have any details.