Yes i receive longer requests most time through airbnb and propose to work "off-line" and do a more thorough background check if i see fit and rental agreement, but i need to rework the agreement to be more specific for the "longer short-term" needs.

Pardon the newbish post, my financial strategy needs reworking and I am hoping for some feedback here to help.I am in the process of my buying my partners stake in our  short rental in Maui. 

(Looks like only one blue door back there.)So, I'd go with those who say convert it back to 4 2-bedroom units and rework the numbers.

.* If there weren't any permits to begin with, you can expect rework because I assure you... the work wasn't done right in the first place.

Having a business degree I am able to get in the financial/business field of RE working on leasing / RE financing after couple of years as well.

I thought about converting it to a 3/2 but there really isn't a way to do that in this house without some major rework. 

I will re-work my expenses and see if this deal makes sense. 

I never really thought about that but now I will have to rework my structure for different loan options.

Reworked the layout and renovated to make prettier and more functional.

It will be interesting how this strategy will have to be reworked in a down market, as you are all saying.