But I find from personal experience and from my buyers' Airbnb experience that it's a bit of a hassle trying to get guests to rebook at the new listing.I don't know how strict Joshue Tree is at enforcement, but in Denver and Colorado Springs here, you could probably get away with an STR listing for three months without the license.

The challenge was balancing the relationship between landlord/tenant and a personal/friendly relationship.

Yes I have known it to work because the owner is not a push over, enforces policy and can make it run good......however, do you have the right personality to do this, AND if you move out can you continue to have the house run smoothly with no one in charge.  

With respect to paying $44k off on your HELOC, I personally think that is totally fine and a great start. 

I personally started in my local real estate market in Columbus Ohio.

Make sure your personality matches your path.  

Personally I like the Section 8 program when the property is located in a super poor area with a ton of blight and crime.

Balance data with personal priorities.

Personal finance is as much behavioral as it is math.

@Jason Weidmannit's only solid if:1) you pick a market that you can go to in person and build a team first, and 2) you recognize that RE is a long-term investment, and you may have to wait 5-10 years, or longer, before seeing ANY return.