If you decide do sell to reinvest the money in something better, are you comfortable taking a loss given the amount of new construction condos selling at a discount you'll have to compete against (and buyers typically prefer a new property unless they urgently want to buy).4.

On the other hand,   there is a non profit in Hawaii called Reuse Hawaii that has a bunch of good stuff at a discount - https://www.reusehawaii.org/. 

We build for a discounted rate on a retainer based model.

4) Seek to help them solve their problem5) ask them what they need $ to get out of the house, and evaluate if you think that's possibleI'm learning to ask a tremendous amount of questions and am finding that I can keep the conversations going far longer than me offering my "insight", I'd encourage you to door knock these people and have a question based conversation so you can learn as much as you can about the property and make your decision on your course of action after that!  

We also give our LTR tenants other rent discounts like taking the trash to the curb on trash day for the STR units so that everyone is incentivized to help the STRs perform well. 

I loaded up on things I had on my shopping list and got them for historic discounts.

@Chris Seveney could you help me understand what kind of discount I should expect to see due to the condos being non-warrantable and not qualifying for conventional financing?

The most southern OR city of Brookings offers tremendous value, and the difference in taxes, insurance and associated carrying costs for crossing the State Line are considerable in comparison. 

Next day she did this: send me the power company's rejection of discount for her electric bill when the house's thermostat is not smart one.

Biggest problem is that managing a Turo rental is more hands on than managing an STR, and is more difficult to do remotely.But if you can find a way to do that work, you've basically got two businesses where every customer for one is a free, super valuable, super targeted lead for the other, with the opportunity to offer a bundle discount to close the deal.