The agent recommended I talk with my current agency and get the renewal adjusted to reflect the property was occupied.I took the advice and reach out to Goosehead (my current agency).

My recommendation for anyone is to educate yourself, whether its Hawaii or elsewhere, because if you are aware of how STRs are regulated in Hawaii, this is far easier said that done.

Should I recommend a lawyer to my client to assist with the financials and license / permits or is that not necessary?

Of course, not as directly labor intensive as what you are embarking upon, good luck in your endeavor.Amazon.com: The Hands-Off Investor: An Insider’s Guide to Investing in Passive Real Estate Syndications: 9781947200272: Burke, Brian: Books

Looking for recommendations for a lawyer who can help us close a multi family deal in the area (1031)thank you for any recs!

Quote from @Brian Jackson: Quote from @Marty Neville: Just reviewed my transaction history from my bank which confirmed my property manager has not distributed rent for 12 months, I have requested a full disbursement.

Probably recommend getting a good property manager.

I don't recommend this approach as standard operating procedure, but in that deal, my first, I was somehow able to walk away with a $30K profit.  

Hi all!  I am expanding my vacation rental portfolio from 1 to 4!  I'm acquiring 3 cabins on a piece of land in the Finger Lakes.  They're already set up to rent and they're almost completely booked for the summer alr...

Jane -- I would recommend narrowing down a strategy in regards to importance.