You need to weigh out the costs, benefits, and drawbacks of the different scenarios such as keeping in your name, putting in LLC, forming a trust, etc.I would also suggest reviewing your leases, etc. with the CPA and Attorney (might have to be a different attorney that specializes in Real Estate).  

@Kristin VegasYou can but like others have pointed out there are drawbacks to this strategy.

What do you think are the potential benefits and drawbacks?

The drawback you have to fit "in the box"; 20% down +, excessive reserves requirement, specific restrictions on tradelines, assets guidelines, DTI under 43%, owner occupancy etc.. if you are open to ARMs you will have a bit more options..Also need to consider the type of property - if condo/condotel banks might not finance at all.. there are many factors to consider we do have some good outlets for jumbo, would be happy to review your scenario and give you a quote.

There are benefits and drawbacks to a high vacancy rate in the rental market.

There is nothing much to do in there apart from the beach and partying and therefore there's no drawbacks to be in an all-inclusive and no advantages to be in an Airbnb.

Hey Adam, you aren't missing anything besides the drawbacks of the Section 8 program in general.

Given your goals, the main drawback with these is that you cannot live in the property, so house hacking is off the table. 

The drawback of relying solely on MLS, realtor.com, zillow.com, or similar listing sites is their widespread popularity.

The drawback to that is people looking for houses get lumped in with people looking for rooms, etc.