For now though my dad and I were talking about him getting a property in Miami that I could manage with him and for a cut and for some first experience.

One is a house, the other is a piece of land that has a condemned trailer on it.

In my many years of this (property management company for over 20 years) I have dealt with similar stuff a handful of times and I still get the pit in my stomach and sweats while my stubborn side says do not cave in when we know we are right.

one i self-manage. 

It is about 100 ft to the fence of the pond from the back of the house.

As long as you have the right team full of deal finders, contractors, lenders, and property managers, it's a great strategy to scale your RE portfolio.Good luck! 

I own a house free am clear that needs a lot of work (80k).

A few deals fell through because of varies reasons, but ultimately we had tons of action on the houses and eventually found the perfect buyer.

On the left hand side of the house, can you make a walkway over the back roof and have steps that come down the back and wrap the corner onto the 2nd floor egress? 

We added value by re-doing the whole house, installed vinyl floorings, rebuilt 2 and a half bathrooms, re-painted the whole house, replaced all the hardware in the house, installed new lighting, ceiling fans, re-painted the kitchen, and completely remodeled the upstairs.