Here's my question, I'm looking at purchasing a 3rd property.  

You'll have to make assumptions and have some fear when you move on a property.

I would be very hesitant to buy a condo as a rental property. 

My partner and I are currently hold 2 properties in the Glendale area that have done quite well.

So maybe consider getting a property outside of Oakland?

You can also negotiate the buyer's agent commission and sign a buyer-broker agreement, which ensures they represent you and assist in finding properties that meet your criteria.Best of luck!

I have a 4-unit property up in Cape Coral, FL that is currently wrapping up construction.

So i found a house that has tall ish grass and a broken/open window with no mailbox at the location and i was to buy this property for my first house to live in for a while then eventually sell.

I have a long term tenant moving out of a property in January.

Yep, I've seen that with my clients' STR properties in Wheat Ridge and Arvada, just outside of Denver.