As a local we enjoy the tradewinds maybe once every year.

Because that may sway who and how you interact also.Plus what kind of money are you bringing to the table to do this, are you broke and hoping (it's purely an academic exercise) or do you have some De-naro to put into a project(???)

I am very fortunate to say that I can generator about $800 pure cashflow from this investment.

As mentioned everyone's strategy is different, I'm risk adverse & enjoy liquidity.

If the answer to the last question is because they would rather stay at home and don't want to get a job or they have a job, but want to 'enjoy' their lifestyle and not be 'burdened' by bills, then it is time for them to grow up and move out.

So, I accepted modest appreciation (doesn't really look that modest since about 2020, honestly), and enjoyed a steady income. 

If your network likes the pure equity play, you should offer that.With the "debt" financing, are you planning on using this as your mortgage, with no "traditional" mortgage ahead of it?  

If I were you, I'd keep enjoying that income and manage it yourself - thus increasing it.

But like @Lucas Carl said, life might be way easier if you make your money here and enjoy a stress-free vacay in a prime destination.

But he said, "I never want to have another month like that because I didn't have time to enjoy my life".