The most important question you ask an off-market potential seller is "Where are you going when I buy this house?"

I’ve heard great things about your meetups, although I never had the chance to make it out to one.

Think of it this way.

Quote from @Elizabeth Rose: @Josh Bowser this tip of doing a quick search on county GIS or software to see if homes in a neighborhood are owned in personal names or LLCs is gold, thank you!

FROM THIS POINT - what usually happens? 

Hi, I would highly recommend reaching out to @Michael H.

Unless you are a seasoned real estate investor with professional title searching skills, I wouldn't do this.

The best house hacks cash flow from living in the smallest and renting the biggest so you need to work out all the scenarios that could come up.

In this market, I would definitely list with an agent and not do FSBO. 

If the R2O buyer gives notice on their current place and your deal falls through at the last minute, those tenants would be scrambling to look for a place to live.I second this, not a good luck to just rush something through.