They focus on golfers and supplement it with the beach atmosphere. 

I've had a lot of success with my property manager's going after Mid Term Rentals to supplement Short Term Rentals.

The comical part of the media coverage and general outlook from proponents is that somehow LESS real estate (buyer agents) = reduced fees.

Ultimately I'd like to at least do a house hack per year and supplement it with some other properties along the way

You will pay a higher interest rate and need a bigger downpayment.What you need is good STR insurance with plenty of coverage to protect you.An LLC offers some protection with contract issues (like kicking someone out during their stay) vs negligence, which is what you need to watch for.

It can help safeguard your personal assets in the event of a lawsuit or liability claim that exceeds the coverage limits of your primary insurance policies.Tenant Acceptance Policy: Implementing a thorough tenant acceptance policy is crucial for selecting reliable tenants who are likely to pay rent on time, maintain the property, and adhere to lease terms.

However, I also see it as an opportunity to potentially pass on risk (maintenance/upkeep/repairs) to an Airbnb host, assuming insurance coverages work out, and/or ask for a premium on top of what I listed the unit for.

.- You need supplemental insurance to protect yourself.

Just wondering if anyone has done this and what safeguards (contract, insurance additional coverage etc), if any, they felt were necessary, and if they've had any unexpected issues.  

Lost income is a core coverage of a landlord policy.