For older demographics, consider the availability of medical centers, entertainment, and restaurants.Buildings/Permits: Assess the city's growth compared to previous years.Determine if the city can accommodate future supply.Government Regulations: Examine the city's efforts and the type of businesses they are targeting.

Last time, we pressure washed the houses (they wanted $175 each home), painted outdoor porch railings and exterior doors, stained the decks, etc.  

Yes TV gurus are just for entertainment.

Their place is in the Panorama Park area. 3/2 fully remodeled with a salt water pool (entertainers pad for sure).

This can save you time and money on property maintenance.Amenities: Many condos come with amenities like gyms, pools, and security services that can be attractive to potential renters and can help you command higher rents.Location: Condos are often located in desirable urban or suburban areas, providing easy access to job centers, shopping, and entertainment, which can attract tenants and appreciate in value.Rental Income: Renting out one or more units can help you cover your mortgage and potentially generate positive cash flow.Steady Demand: In areas with high demand for housing, condos can provide a consistent stream of rental income.Potential for Appreciation: Condo values can appreciate over time, potentially increasing your overall return on investment.Cons:HOA Fees: While HOA fees cover maintenance, they can be costly and eat into your rental income.

Chattanooga has a good scene and has consistently been named one of the best outdoor oriented cities to live in the South.

I'd like to entertain the thought of an established STR / AirBnB in a great neighborhood in Chicago or in the city.

It's proximity to the outdoors, "Northern" feel, and good dining/entertainment scene lead me to believe that, soon, more of the those UMD graduates will be sticking around.

It was RWN, Judson and Lynn Voss, and then later Lifestyles Unlimited podcasts that provided much of my listening entertainment that kept investing fun for me.And now I have BP.

@Adam Juodis, have you been getting more entertainment value out of your question than you bargained for / wanted?