If you are married, put the debt for the family house in only one person's name.

Attend open houses to understand market trends.

In addition, a strong property management company will tackle all aspects of marketing, application, ensuring resident satisfaction, fair housing, handling late payment/evictions, renewals, etc. 

from a laptop or mobile phone on one of my SFR's (internet must be hooked up, but most tenants do it anyway and like to be able to monitor the outside of the house remotely, even if there's nothing going on.)

My wife and I got a duplex downtown and are house hacking one unit. 

Being boots on the ground out here, seeing the state of some of the homes here both on and off the market and knowing the price of housing in the area, I am confident that I could be successful in flipping homes here. 

As a broker, you’ve already got a strong foundation, which will give you an edge in finding and structuring great deals.Since you're in Chicago, have you considered house hacking as a starting point?

If one of the greatest investors of all time believes stocks are overvalued, this may be an opportune time to shed some risk and move into a more tangible asset like real estate.The Rochester housing market is a great place to consider for investment.

Im no legal expert but belief if you get foreclosed on 2nd home and you still owe money they can come put lien/go after first house.

Sounds like you should go the house hack/FHA route.