Insurance and taxes have increased but Im still clearing the same amount.

I would probably just keep the security deposits in the same new account that I would paying the bills with.

To illustrate the other side, the rest of the island (outside of these resort zones) has historically been a place where owners can only do MTR's - 30 day + stays, but new legislation just got passed and it's looking like a minimum 90 day stay will be required.

All this means is that you take over the existing mortgage with the same lender but using your credit, income, and assets (the same way as you would obtaining a new mortgage). 

Everyone else faces the same problem. 

Then, with so many people in the same situation, the housing market started to get flooded with houses.  

On market 120+ days.

You learn something every day doing this.

I'm brand new to the game and still learning oodles every single day.

They will not use the income if you don't have those lined up by closing.Tons of people do this, and I also did the same thing earlier this year.