Some car companies don't allow transfers of their cars shortly after they are released.

In short, my membership fee bootstrapped me such that I have more than doubling my net-worth. 

For example, most real estate deals throw off significant depreciation which can provide a very nice short to medium-term tax shielding benefit.

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

Start by leveraging what you already have—consider tapping into equity through a HELOC, house hacking again with an FHA loan, or increasing cash flow by converting a unit to a short-term rental.

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.

Consider different strategies like mid and short term rentals as I believe the Portland area would allow for success in both (although I have heard Portland proper is tough on STRs).Best of luck!

With the fires, labor and materials are going to be in short supply.

The bullet in the response that is standing out to me is:"(7) The accessory dwelling shall not be a short-term residential rental, as defined by City Code section 3-2-152(a)(2), for a period exceeding 120 days per calendar year."

BTW - AirBNB is a platform where you list your Short Term Rental.