If you choose San Diego, you're in for a treat since the beaches are top notch!

The management company will work for you, but if they treat tenants well you’re less likely to end up in a dispute.

But she kept treating my friends and family members as contractors who come to my house to fix something etc.

Treat it like your interviewing them.

I'd try to treat them with respect when it comes to ending of lease/rent increase, make your offer, see how they react.

In addition, I would make sure you have created a rental criteria that outlines income and credit requirements as well as how you will treat those with a criminal background or eviction history.

I know CAP Rates are only a quick reference, but how do you "quickly" factor in the expenses to rehab a property showing high CAP rates, or do you treat that like you would on SF flips/rentals where you deduct rehab costs from the Purchase Price (which I don't think is how it works)?

I told them upon moving in that they are to treat the house like their own and repair what they break. 

How do I treat the long-term capital gain (or loss?)

I personally prefer Fort Lauderdale and feel clients would probably treat the property better, as Miami has more of a party vibe in regards to tourism.