Unless you want your "friend" to take ownership of the property should something happen to you (or vice versa), do not hold title as joint tenants. 

Since there’s no production expectations from the company, you are free to captain your own ship.

Neighborhoods listed as trending can have a bad section and vice versa.

Lower risk, lower return, and vice versa.So, I have a duplex around the corner that is under contract at a 7.5% cap rate (estimating expenses to be high) after 3 days on market. 

The way I see it right now is that if I do right by Steve, I hurt Ross; and vice versa.

Would you advise I buy a investment property before a family home or vice versa...

There are plenty of great Section 8 tenants, and plenty of horrible Market Rate tenants (and vice-versa, of course).

I personally think you should invest in an area like Pittsburgh where you can pick up your first few properties either single family or multi-unit at low risk as you can pick up single families in the $50-$100 range easily and rent at a 8-12 CAP and if things don't work out, or you change your strategy (i.e. decide to sell off your single family to focus on multis or vice versa) you can do so easily and for profit in most cases2.

The property LLC allows for customization of every deal (vice forming  LLC that hold Title to each property).Having a multi-member LLC for each pair of you might be a bit overkill, but can be useful if you plan on getting into more complicated structures. 

The best is not the most efficient, and vice versa.