However, if you can find one, I'd jump on it because in my case, one side alone can cover the whole mortgage.

I’ve done the same with one of my properties and agree with everything you mentioned.

With housing inventory rising in many parts of the country I'm keeping an extremely close eye on Oregon Coast listing inventory. 

Of course, every market is different, and labor/material costs vary, but here’s a rough breakdown by rehab level:• Light rehab (paint, floors, fixtures): ~$15–$25 per sq ft• Moderate rehab (kitchen/bath updates, some systems work): ~$30–$50 per sq ft• Heavy rehab (full gut, systems, layout changes): $60+ per sq ft, sometimes well over depending on scope and finishesA quick shortcut we use when walking properties: estimate cost per item (e.g., $6–10K for a full kitchen, $3–5K per bath, $7–12K for HVAC), then sanity-check it against the square footage calculation.Definitely recommend confirming with a local GC, especially with current fluctuations in labor and materials.

You are on the right track, and you will find the right one, even if it takes time!

In other markets like Nevada, property taxes don’t reset at sale and they are capped at 3-8% depending on if they are rentals or homesteads and if they are rentals, how much rent is charged. 

There's no one-size-fits all midterm rental.

He really did a number on us.

There are 2 types of people who dog on Detroit.. 1.

One option I may have is to separate the parcels and sell the standalone ADU as its own SFH (which I am not banking on at all).