I wanted to get feedback on managing short term rentals in Hawaii. 

So, long story short, I would just get an estimate from a firm and go from there.

My plan is to add 2 - 6 shipping container type of small houses and an above ground pool at some point to make at least a section of the property short/mid term rentals.

What are you looking to achieve in the short, mid, long term?

Since it was my first duplex, I thought having one short term and one long term rental would be good.

If I have several options, I would prefer a HELOC with no initial draw requirements (i.e. to establish a literal line of credit that I have no specific short term plans to use), i.e. not something like the better.com HELOC. 

On the other, the prospect of short-selling the homes didnt look so awesome either.

Short term leverage inherently increases our risk. 

I have rented out this home short term before and have been successful but I don't have any experience with 12 month leases.  

Long story short, he couldn't see anything wrong, but said he would have a lot better idea if he could camera the line during the next clog before it is cleared.