The short term regulations vary by county so what is legal in Hawaii county (big island) is not necessarily legal in Maui county Lanai Maui and Molokai NMhappy to offer feedback but it seems like you're actually only concerned with Honolulu Waikiki.also they (the state legislature) just passed a bill like yesterday that requires Airbnb VRBO to collect a short-term rental taxes for vacation rentals legal or not

I got extremely hyped about David Green’s story and examples, I’m determined to model my growth on his, but what is holding me back on a lot of my deals is the cashflow. 

@Kevin Aljic Residing in Texas your options are extremely limited for a HELOC on investment property, to the extent that I still hear that they are not allowed.I might be biased but I feel the easiest route is going to be a cash-out refinance on your investment rental.

Another concern is, it also seems impossible to get a straight answer on whether LIDs are deductible for rental properties; it is clear you cannot deduct them as a property tax if it's a primary residence, not sure about on an investment.

I can see where conflict of interest come in play when working with sellers, but what concerns do you have from the buy side? 

I wrote the post a while back so the rules concerning this type of a structure have actually gotten better. 

The rate you are offering is very low so I wouldn't be too concerned.

As an insurance agent the liability is extremely high and I can't imagine finding any policies that would make it financially feasible.Local municipalities also have regulations regarding short term rentals so that could be another hurdle depending on your city/state/HOA/etc. 

That is EXTREMELY high.

With a 15 year loan, you'll  find yourself with an extremely high payment to make each month.