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.  

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.  

Your best bet is to get on the phone, get multiple opinions, multiple quotes, and make decisions on the type of build before pulling the trigger.

the key to investing in these types of deals is just like you just said.. you can lose the money and not change your lifestyle..

Have you considered what property types or markets you're interested in?

3. what type of deposit / reserves can you provide in case the monthly rents you receive do not cover the rent you pay me?

If you kept the property, and accumulated the CF/yr, it would take you 25 years to get that same equity that's sitting, frozen in your property.Also, if you cashed out and used that same equity as a DP on different RE, at 20% DP, that equity would buy you $2M in PV, not just $700k,...and, I'd be willing to bet, you could find new RE that would have a yearly CF well over $20k/year.On top of that (remembering my initial statement above), any appreciation applied would be applied to $2M, not just $700k. 

Regardless of the type of lender you work with, building a trusting relationship is crucial.

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

Best bet is to carefully analyze the zoning maps and regulations or just call the town and ask.