It may be more profitable in the short and long term than a duplex. 

Any other suggestions for less-seasonal Florida STR markets?

I would mention here that a typical condo or single family does not qualify for the Act 60 TOURISM tax credit (which gives you up to 40% back)  - the project needs to meet certain qualifications as a guest house, hotel, villas or bed & breakfast - it can be as little as 3 rooms.  

Obviously I would like to give them plenty of time to uproot their lives, but also want to balance being too generous or giving away way more than is necessary.Thoughts? 

If you are already on VRBO and Airbnb, you have more than enough exposure to stay booked.

The biggest reward of owning and managing vacation rentals is much greater than financial; the friendships I have made with people around the country are priceless.  

I was so excited when the attorney released the bid amount on Friday at way lower than I would have thought!

In a “nutshell”What can work - partnerships where each person brings a different necessary asset (knowledge, experience, time, capital, credit) to the table, the responsibilities, rewards, and expectations are clearly spelled out, legal documents are created to head off disagreements, and the parties are compatible.What doesn’t work - partnerships formed by two or more inexperienced people looking for “comfort” rather than going it alone, and anything other than the above. 

If your rental income exceeds your mortgage debt than you have left over money at the end of the month (cash flow), you are in more debt but your RE debt is being covered and you have something left in your pocket

If fixer upper then usually offer 70% of ARV less repairs.