There are organizations that can provide the family with rental assistance; every municipality has one - and the assistance covers utilities as well. 

Any recommendations on how many rental properties per LLC?

I'm curious of the current market demand for student housing and appeal to rental investors.

I would love to get a condo down in Miami to have a as a forever rental, but it's just so hard for me to pull the trigger.

Miami Rental Market Update: Rents Drop $200 as Affordability Remains a ChallengeMiami has officially ranked as the second-most unaffordable city in the U.S., but there’s some good news for renters: local rents have dropped to a 3-year low, with decreases of up to $200.

Your mentor’s advice about starting with a rental property is solid, and a duplex could be a great option for house hacking.

Personally when buying rentals I tend to buy in neighborhoods that I feel like I wouldn't personally mind living in and when I look for tenants I try to look for people that not only pass my screening but also I personally don't dislike.  

It seems like it would be great to flip one property while planning on getting another one ready to add to my rental holdings.

I have 8 single family rentals in 2 single member/pass through entity LLC's. 2 states.

And I agree you'll probably feel a lot better having your rentals in your backyard.