And an important side benefit is that you'll have the guidance of a broker who will keep you out of trouble by making sure that you follow the law to the letter. 

The minute someone is simply a passive party, this can get you in trouble.

Once you build a relationship with a broker they are more likely to send you "off-market" deals which tend to produce the best returns because they are less competitive.

We did not like booking.comWe had trouble integrating it with our other systems, and did not like that guests don’t get reviews so there’s no accountability.

Other wise.. if you want to earn money in real estate get a license and go to work on a high producer team and GET PAID to learn ..

Tourist town sounds like Airbnb is your best revenue producer except you sound like you’re interested in monthly’s.

Surprisingly it seems like they aren't having much trouble gaining traction with their current model.   

Eating our own fruit, is a big kick.  200 pineapples in another 12 months.  200 Coconut trees producing in another 5 years. 

Where people get in trouble in HELOCs is when they use the HELOC to pay for liabilities (boats, cars, bills, etc).

I was actually much more focused on and concerned about myself getting into trouble for knowingly allowing too many people to reside in the unit.You are correct, the real reason I need them out is to renovate.