Your best bet is to keep liquid cash and avoid PMI.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

You second property will rip I bet.

But, I bet-ya it's also effective.  

You can talk to the bank about a loan; however, my bet is they will want some form of contract and scope of work and will only pay him at set milestones.

Honestly, upgrading to a commercial-grade stackable setup like Speed Queen or Maytag might be your best bet.

I bet $1 this a bot. 

If you could furnish the rooms, I'd say that is best bet for cash flow.

Again, knowing nothing about this particular company, my bet is that type of company will require money up front just to consider whether they can help you out.  

Rejects County’s Allegations That Lenders Engaged in ‘Integrated Equity-Stripping Scheme’14. https://www.pinecountynews.com/opinion/columns/protect-farmers-from-equity-stripping-scams/article_e2cfa266-7caa-11e9-b749-830948f9d469.htmlEquity stripping scams were particularly prevalent in the early 2000s.