What are the challenges of passive investing as opposed to traditional real estate investing? 

The red flags of managing from a distance and hiring a property manager are legitimate concerns that make it more challenging.

Each week, I personally analyze the MLS, leveraging my deep knowledge of South Florida’s short-term rental market.

Successful BRRRRs are challenging enough to do local to you.  

Quote from @Michael Challenger: I would connect with local people at meetups, that might give you some contacts for private money.

One of the challenges of beginning wholesalers is they do not have a buyer's list.

Whether these factors outweigh the challenges is a personal decision. 

LTRs with long term conventional financing and standard management aren't really cash flowing anywhere right now. sure, there are lower cost markets that look better on paper, but there are costs associated with those supposedly cheap markets as well - deferred maintenance, more challenging tenant base, higher cost turnovers as a percentage of the rent.2. i wouldn't pick a random market thousands of miles away based solely on statistics or numbers. 

Together, we can harness the power of technology and creativity to make significant strides in our personal and professional lives.

I 100% agree with the intent aspect and that is an important premise, but the fact is in this particular situation intent for it to be personal use has been confirmed (by way of a public post).