Need a little more information to throw out a few ideas. 

Low risk investments sell at a premium, that's the whole idea of cap rates.

., and I still love Cook County because I have a solid team and underwrite deals properly.I think @Paul De Luca nailed it on the head, though - it seems like you are quite risk-adverse, so maybe given your risk tolerance, it's not the best idea, but if it were me, I would not think twice about it, and find a rock start property manager who knows exactly how to vet tenants.

I think house-hacking is a great idea and I would be more than happy to help you with the financing.

Additionally, it's a good idea to connect with a Property Manager early on.

You have a head full of ideas, and that is a good thing.

I have no idea what you mean in regard to lending to my cousin, but it doesn't matter. 

Great community to bounce ideas off of as I build my knowledge base.  

Lets say the idea of higher mortgage and more debt pulls you back from making a move.

After they book, it's still a good idea to use the platform app for communication because then the platform has a record of what you and the guest have said, in case you need it when a guest does damage and admits it to you, but later denies it to the platform.