In addition to my surrounding area of Bridgeport, I am also open to looking in New Haven County, Middlesex, and Hartford as well as an out of state market (Detroit, MI). 

Ditch the cheap shower surroundPlease don’t buy that cheap five-piece shower surround that you saw at Home Depot or Lowe’s.

I spent time in the league and have since built my real estate portfolio and started a real estate agency and property management company servicing Indianapolis and its surrounding areas.

You’re surrounded by a support group I never had, and that’s a positive.

Indianapolis and surrounding areas often offer strong rental demand and reasonable property prices, so you’re definitely looking in the right place.For neighborhoods in Indianapolis, I’d suggest checking out areas like Fountain Square, Bates-Hendricks, and Irvington.

Yes, you bought what seems like a good deal on paper, but in reality, you own an old apartment building in a neighborhood with poor security, possibly surrounded by long-vacant shops, streets piled with garbage, and a poorly managed community.

Denver and its surrounds have particularly active markets and a lot of active individuals offering ancillary services so I'd suggest you research those available services you're looking at offering to help you get an idea for what is well covered, what is lacking and what your competitor's pricing looks like.

However, there are several up and coming thriving communities surrounding the Texas metro centers that may be worth looking into.

While cash flow can be limited within the downtown area, there are still excellent opportunities for cash-flowing rentals in surrounding regions.

I agree with @Gregory Schwartz that as long as your eyes are open, you are asking good questions, you have resources and have surrounded yourself with a good agent and PM, take the leap and learn as you go.