To me STR and hotel caters to different groups of travelers and so despite competition as long as the travel demand of Hawaii remains (as you pointed out is a robust assumption) I think both will continue to do well.  

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Neighborhoods like Logan Square or Albany Park have seen growth in rental demand, making them potentially good starting points.

These are what we call "A-class" markets—areas with strong fundamentals, high demand, and typically excellent long-term appreciation.

you are right on both counts - it is saturated and there is tremendous demand within all asset classes / niches, AND real estate is constantly changing hands and there are still deals out there. 

Do you think that demand will be high for something like that? 

When I partnered with friends on a multi-unit property a few years ago, we chose individual umbrella polcies from our personal providers.

Multifamily doesn't need any more pressure/demand since cap rates can really get low when too many people pile in, but I have to say that commercial real estate (including large MF) and other types of passive investing (mobile home parks, storage, etc.) can really make like much easier.

Would you demand they pay for the fix?  

.- Tenant submitted a work order for low water pressure in 2 bathrooms- Tenant submitted a work order because the garage door doesn't close all the way and left a 2-3 inch gap at the bottom- Owner initially refused to address either work order- Owner demanding the tenants place furniture pads on each piece of furniture- Owner calling multiple times to speak through the work orders, asking when they've been scheduled, calling a couple days later requesting the invoices- Owner calling because they want to access their storage in the basement so they can remove several pieces of furniture being stored- Owner now emailing requesting multiple property inspections throughout the lease cycle- Owner questioning my experience and relative PM knowledge because I'm not following up with her in a timely manner (the following day after the work order)Keep in mind, this is 2 weeks after the tenants had moved in and the tenants are very happy in the home.This is something we see on a regular basis.