All in all, I feel like my personal risk/reward is pretty high and I can stomach a drop in my net worth well, recover completely, and make it out ok.

If you're really ambitious, office to residential conversions and if you have an iron stomach, office is in "buy low" mode--question is whether it goes even lower and how long will it take to be able to "sell high". 

If I had to stomach half of that I'd turn everything I own over to a PM or sell it all 😂

In my experience most buyers are spooked by having to do anything more than changing a lightbulb, so first I think you need to decide if a rehab is truly something you have the stomach for.   

What's your appetite for risk and your stomach for stress?

Anyone else sick to their stomachs of having to WAIT??? 

I imagine it would be hard to find a property manager that would stomach that, and I really would prefer using one.I'd also look into doing ADU's on the land to increase flow, but my understanding is that is illegal here for some reason.I really wish we could search these.I am interested in any thoughts you have on this.

If you can't stomach having your home at risk then you should probably own it outright.

Narrow stone walls stomach-high on either side, then open crawl space, then layers of floor boards.

Even if the property pencils out strongly today the potential downside (economic slow down, recession, etc.) is to great for me to stomach.