If you can find a condo with an active HOA and one that has a healthy reserve and is run well, condos are amazing investments.  

Would like to grow a healthy cash-flow portfolio in the next 5 years to supplement (or completely replace) retirement.

I'm in analysis paralysis... but I think it's definitely necessary for a newbie to calculate and proceed with healthy caution.

Over time, the stock market will provide healthy returns, but it comes with lots of volatility (ups-and-downs).

If all of the units are dated, assume a healthy number for regular repairs, and assume at least 1 major and 1 minor appliance to be replaced yearly for the whole building. 

The variation above makes it very easy to buy thinking you are getting one thing when you might be getting another because there can be 1 mile difference and 10X average home priceIt is a rare combination of a growing, healthy economy with MANY affordable housing options.

LuThe midwest region offers healthy returns. 

I'm a doctor so these conversations come naturally to me, it's just that your diagnosing the home owners needs and wants rather than the patients health.  I

Pullbacks are healthy and a balanced market is good. 

What sort of due diligence did you do to make sure the HOA is healthy and there are no unexpected surprises down the road?