Bigger Pockets is a great place to learn and connect with fellow investors.What was the key factor that helped you make the decision to invest OOS? 

Call a couple local property managers (I’d suggest key property be one of the calls.

Whether it’s a multifamily in Boston, a value-add deal in Worcester, or an investment property in Lowell, the key takeaway is the same: the listing price is not the purchase price.Here’s an example I use with clients: If I sell a 3-family for $650,000 and list it at $599,900, suddenly, it looks like it sold for $50k over asking—“Wow, it must be a great deal!”

So let’s examine the key factors that can help investors sort through these remaining subset1.

I'm not against innovation but every point you raise is pre-existing or illegal/ against regulations. 

Pass Code to open a Supra like key box.

And having reserves or cash flow is key - will help you absorb any unforeseen situations.

the key to investing in these types of deals is just like you just said.. you can lose the money and not change your lifestyle..

I will do my homework on long distance REI (even tho the markets are 1-2 hours away), but have a couple questions- What are some of your key metrics/signs you use when identifying a new market?

Market is not generally fast moving so having a good agent is key.