And by higher risk I mean higher risk of tenant issues  generally older homes with a lot of long term differed maintenance. limited opportunities for any REAL appreciation . 

For example, theirs is relatively less maintenance and comps are easier to find.If you're looking to maximize returns, typically SFH and multi family would yield better returns and wouldn't have the risk of HOA fees increasing.

In the end it is about your risk tolerance. 

@Steve Morris are you assuming the risk is high based on the reward?

Buying a rental property while continuing to rent is another solid option, but it might come with more risk since you’d be juggling rent and a mortgage.

Maybe you like the risk, but good and great investors don't try stuff like you suggest.

You need to be careful around the risks of sudden price changes, market stoppages and watch for transaction fees.

Additionally, most of these properties have very favorable interest rates, so I’m hesitant to refinance and risk losing the cash flow they currently generate.Last year, I sold one property to invest in a STR in Orlando to diversify and move into a better asset.

Quote from @Levi Perl: The purpose of background screening is to determine a level of risk, and then you decide if you can mitigate that risk.How does a DUI conviction from three years ago impact the tenant's ability to pay rent or maintain the property?

If they want to severely overpay, cool, but as others have said, the risk of default in this case is probably high 98th percentile.