We talked to a lawyer and they said the lender should be able to provide documentation that "due on sale" is not applicable. 

I started with Ken McElroy's books, because 1) clearly he knows what he is talking about given his track record and trajectory and 2) because I had easy access to them. 

I would talk to some lenders and see how that would look and what you would be approved for. 

Longer lead times I get alot of intern inquiries which can be fine but income wise they aren't as strong a candidate.  

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.  

It sounds like they have been paying, maybe talking to them about your concerns can help them better meet your expectations.

I haven't posted in a while, and most I talk to have stated the slack in the market and slowed down with others who have backed off on buying/investing.

So when I hear other investors talking about how adding ADU's adds equity, you're telling me this isn't really a common experience?

I love that you're focused on a niche that isn't talked about too much.

You also had at least 3 blinds to replace at the 3 bed place.Again some of the stuff from the second place should have been billed to the tenant (ie reattach thermostat, missing blinds, etc).If you want to have the ability to do the repairs yourself, then talk to your PM; but you need to do them quickly to make sure the place can be ready for the next tenant.