BTW, I am not disputing you, just playing devil's advocate and wanting someone to challenge my thinking. 

@Pratik as @Neil Narayan mentioned, cash flow is very challenging due to the property values, property taxes, and soft rental market.

When it comes to the STR game, differentiation is critical, and that can be challenging with a 550 square foot oceanfront condo. 

Challenges?

It is challenging to build an underwriting box for something that fell outside an underwriting box.

I’d challenge you to go approach any sponsor and and ask them what percent of the deal they’d take.

In my search, I've noticed that many positions require proficiency in Yardi.I've been actively looking for effective ways to learn Yardi, but it seems challenging to find suitable training or courses online.

@Samuel Coronado - the challenge is that there will likely be a very small number of renters looking for a house that size, as well as that can afford a rent amount that high who won't just buy otherwise. 

Our portfolio currently cash flows, but cash flow isn’t our top priority right now since we plan to use this portfolio to supplement our retirement in 12 years when I leave the Army.My biggest challenge is committing to an out-of-state market.

Challenges?