Doing a deal like this is not a test the water situation you can just walk away from it when it gets tough, or when you grow tired of it.

The problem with that is two-fold: first there are likely existing assets that are not replaced that qualify for shorter asset lives so you're leaving money on the table, and second you have no cost basis for the removed assets replaced in the remodel as they're intertwined with the initial building cost basis so you'd technically still be depreciating retired assets which is tax fraud. 

So from 2025, I’m thinking of living upstairs and running bottom floor (half of total RSF) as an STR.

My goal is to live in this first property for at least 12 months (but realistically a few years) and have a roommate in the second bedroom to help offset the net costs.

However, there are tenants that have lived in at least one of the units that have been there for over 20 years.

This could be attributed to the higher quality of life, better schools, and overall satisfaction with the living conditions in the more upscale areas and there is no thing like 0 vacancy. 

Even if you purchased your home at the very tip-top of the market before they dropped by 19%, if you would have simply paid your mortgage payments, mowed your yard, and stayed in the house for 6 years (you had to live somewhere during that time), you would have made money on your home...and that was the worst drop recorded.

Live with it for 6 days until the end of the month and then raise the rent 30-50% or just don’t renew.

Aloha @Michele Nakapalau -  I live in Mililani. 

There are 2 beds/2 baths/1 living room upstairs, and 2 beds/2 bath/1 living room down stairs in the fully finished basement with a separate walkout entrance.