Its an awkward question, basically Im asking for a legal bribe. 

Same basic theory of living in your first rental but done properly without the messy part of being in the basement bootleg rental, having shared areas, utility issues, potential HOA restrictions, awkward meetings in the laundry or entrance, etc.Best of luck

I can imagine this being a very stressful/ awkward situation, one that I might be experiencing soon and I'd love to hear people's thoughts.

This is a guy who reads the books but will never invest on his own, because he's painfully shy and awkward.

It's also easy to manage a house right next store, so great for learning (though if you have to evict them it may get awkward for a while). 

My primary residence, which will soon become a rental property has an awkward driveway (they raised the road in front of the house).

This was verified when I dug down on the interior to remove the garden spigot that original builder buried 5 feet down and connected it with an awkward shut off valve that required a key that was 3 feet long!

There is a super awkward 4th bedroom and very tiny dining room.

Frankly, I attended a few networking events while I was at the university, and found them a bit awkward and of limited value, but you all sound like a good bunch so far.

If not, you run the risk of losing your friend and having an awkward co worker.