@ Theresa, The ONLY doubt in my mind NOW is if this -My lease is a standard zillow generated lease.

I recognize there are other ways I could invest this cash (including another property) but I am being mindful of levering myself out too much in the current environment where job losses are more common in my industry (tech).

I think I've talked to maybe 2 tenants on the phone so far, and I didn't mind because there's a lot of scams online.

Keeping insurance and ownership in mind, what is the correct day to start the lease?

But no doubt we have to keep in mind as stated this site caters to a lot of folks starting their journey so to us who have been on the site for a minute or two it seems repetitive but to the new investor its not they dont know what they dont know.

It’s such a great resource for learning and connecting with like-minded investors.

While using QuickBooks it is a mind set and you have to accept the process and procedures to use it as a real estate and property management software.

@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

What is your motivation for an STR and the Hawai'i market?

Keep in mind if there are economic shifts that you are seeing, so is everyone else, so you may have missed the boat.