You should watch for the load bearing walls, you should also make sure that all apartments have two egresses, and that they are up to the code of the township that you are in.   

It is a load bearing wall not retaining wall.

Please bear with me, and spare any ridiculous "that's the dumbest thing I've ever heard" comments, LOL.

It's a bear to travel through there in the high season.

Down the road when I'm more comfortable I can see myself going out of state, but I don't think I want to for my first experience.If I'm totally honest, I'm probably too risk-averse to make my first property(ies) outside of comfortable driving distance (max 3-4 hours), leading me to look in places like the high desert (Joshua Tree, Yucca Valley, etc) or mountain destinations like Lake Arrowhead/Big Bear. 

On the other hand, if you are tearing out load-bearing walls, redoing the plumbing and electrical and adding a new porch, you would need a different coverage. 3.

Simple rentals take 20-30 years to bear Fruit. @5 year ago prices, maybe.

Paying them separately gives you a few extra months of letting the money sit in an interest bearing account but that's about it. 

In which zip codes would that be ? are

Typically bear markets on Wall Street start before there's an obvious catalyst.