Since you're in Destin, you might want to check with local firms that have experience with STR-heavy communities, as they’ll be familiar with the risks and requirements.

As mentioned above get involved locally. 

I am left to wonder, though some investors with SFR's are doing it successfully, is the risk too high for the reward?

Specifically, I am interested in learning more about syndications, working with lenders, lawyers, CPAs, and other professionals involved in cross-border real estate deals.

When you buy a property at a time, the risk from the uncertainty is small.

There is still some paperwork involved but significantly less than traditional lending institutions.  

I am guessing a few will say to have my lawyer do it, but the other LLC was so seamless that it seemed superfluous to have someone get involved. 

The cost of a sewer line is the same whether it is on a triplex or a single family home, but with a MFU you can spread the risk.

Key Factors for a Good Seller-Financed DealCash Flow: Rental income should exceed monthly payments (PITI) by at least 1.25–1.5x.Purchase Price: Compare to ARV and market value for fair pricing and equity potential.Interest Rate: Aim for competitive rates; higher rates must still allow positive cash flow.Amortization/Balloon Terms: Favor longer amortization and align balloon payments with your exit strategy.Down Payment: Lower upfront costs reduce risk but should meet the seller's expectations.Flexibility: Seek no prepayment penalties and fair late-payment clauses.Property Condition: Ensure the property’s condition matches terms through inspections.Seller Motivation: Assess the seller’s willingness to negotiate favorable terms.Exit Strategy: Have a clear plan for refinancing or payoff at term end.Portfolio Fit: Ensure the deal aligns with your financial goals and risk tolerance.Vetting multiple deals and consulting professionals is crucial to making sound decisions.

One of the biggest challenges for everyone involved is being on the same page about the actual time required for maintenance.DIY landlords rarely properly track their time when it comes to property management in general - tracking their true time invested in maintenance is where they perform the worst.Investors that hire PMCs are rarely any better at understanding the true amount of time maintenance takes.