After purchase, advised by the City of Lee Summit that the property was intended to be held by the HOA in perpetuity and not by an individual owner/business.

I've owned 50+ rentals and can't recall a rental agreement being perpetual. 

It also doesn't vary based on renovations - its fixed into perpetuity.

Do you think you'll keep doing this in perpetuity?

The key here is to determine what your goal is as you will continue to find yourself chasing new opportunities in perpetuity without it. 

So for risk mitigation, I would like to make sure that its ok to hold the property for perpetuity with the current tenants. 

Meaning do you understand your potential customer, or are you just guessing based on stereotypes.

I know the stock market has been "up and to the right' perpetually for the past year, but don't let it fool you. 

We have learned to step outside of the spreadsheet and look at old Chicago buildings (this particular building was built in 1961) with an eye towards their quality, character, and factors that will make renters say "I want to live there" in perpetuity.

We have learned to step outside of the spreadsheet and look at old Chicago buildings (this particular building was built in 1961) with an eye towards their quality, character, and factors that will make renters say "I want to live there" in perpetuity.