Could I BE any more awkward?)

Frankly, the exact diagnosis wouldn't do you much good even if it weren't awkward to ask, as mental health diagnoses aren't at all an exact science, the rest of the details matter much more as to whether the person will be a good tenant.As for a direct answer as to whether mental health issues put you into a protected class, I'm guessing if they have a case manager, they're probably considered disabled by Social Security or some other gov't definition.

Thank you Brandon for the video, not awkward at all.

It turned out great for me those last 2 years as I became fast friends with my roommates anyways, but for international students with language barriers or someone less outgoing, it might have been an awkward arrangement.I'd try to advertise to groups of friends instead of individuals so at least you know your tenants should be able to communicate well with eachother and I think it kept us in check a little more than if it'd just been 4 strangers. 

I would start off with an investor/properties that are in a different segment, so there isn't an awkward situation where you both want to buy the same property.

what in the world do we talk about to keep it from being awkward?

A common question that always seems to be awkward is "What are you going to do with my house?".

This can be awkward and uncomfortable at times.  

Also if owning property there are numerous little things that need to be purchased that going through normal channels is at the very least awkward.

I know that it's awkward but honestly most GC's will appreciate it.