Lower Greenville/Live Oak/Skillman, Kids Springs, Elmwood (The only one we havent live in),  Medical District , and now the M Streets (ok not so much up and coming, but we got a great property with a decent structure for land value.)I think as new investors, a house hack or two especially with a duplex is the absolute best way to go. 

So, if you're investing for cash flow you will probably need to focus on secondary or probably even tertiary markets.

My children and ex have moved out, and I’ve had to make some essential updates.The property is unique with, in my opinion, much potential for development for AirBNB (not sure how that market is doing), mid term rentals (I.e. nurses or other medical professionals), or weddings and events.I’m new in this space and know I need some networking.

You can find nice rentals in Florida that retirees and medical industry millenials are flocking to.

They are in an area where young medical personnel are located and the vacancy rate is low.

You'd have the cost of fully furnishing the unit, but a 2/2.5 is actually a very attractive unit configuration for traveling medical professionals and digital nomads so long as it isn't prohibited if you're in an HOA.

You can snag Medical/Dental/Law/Pharmacy Students, or some of the new Fellows through various foundations who trying to score a cheap place, $400-$600, in the City(requirement to their employment) but don't have the money to live in Downtown, Midtown, Lafayette Park where one bedrooms start at $1000/month, two bedrooms start at $1300.Check areas off/on of West Grand Blvd, but south of Michigan Ave.Also,Right now The North End is in play, thats the area off of Woodward but south of Highland Park.

You did not have a mortgage on your home until last year, when you took out a $50,000 loan, secured by your home, to pay for your daughter's college tuition and your father's medical bills.

Look into out of state investment in the suburbs of  "second tier" cities as they call it - they all have HUGE potential with major medical/tech companies moving Pittsburgh, Columbus, Cincinnati, CLE all have multiple up and coming neighborhoods that are ripe for smaller flips or generally left aside by intuitional investors

Repetitive, slightly hazardous work causes that over +60 generation to need more medical care.