You get a huge bargain on rent, which is usually the goal in a house hack, he gets a little more of the cash than if the room was empty and he had the added security of a partner in the house mitigating risk.But don't argue about who is RIGHT

Therefore, while I would love the extra time to mitigate risk but not at the cost of the whole exchange potentially failing due to an audit. 

I'd make sure to vet the tenants before hand (background check, credit score check, etc) to help mitigate risk of your new tenants not performing. 

If your lease does not have a lease break clause check your local laws -  but  importantly you must diligently try to lease the unit up to mitigate damages to the tenant....   

Which investment would you be able to assess and mitigate risk on better?

Learn to mitigate risk through screening .

Short Term Goal: I am going to begin by house hacking or with a live in flip in order to mitigate risk while exposing myself to the hands on experiences that books can't provide.

In my mind the whole point of a properly executed anonymity structure is to mitigate risk. 

But generally for rentals, I think just one account (or two if you want to do risk mitigation with staff) is sufficient. 

A partner for OOS is the best way to mitigate your risk though you are not likely to enjoy a great return.