Can I elect to combine these two and take bonus bonus deprecations on both if I can achieve real estate professional status on the property that I manage myself?

Some people, in general, need multiple accounts, eg. one for day to day cash, another for a rainy day fund, another for a play fund, another for an emergency fund, another for a savings fund. 

Take advantage of bonus depreciation now.There are reverse exchanges and other more exotic exchanges but I personally not sold on the concept when the IRS comes knocking.

In my experience flippers make the quality of a city improve, but like @Greg H. said, there is the "you aren't from around here" factor at play.

This isn’t a long term play, so I’m not emotionally attached to the condo or a house, just want to do what makes the most sense.

@Jay Mersfelder sounds like you have some chips to play with to accomplish your goals.

I can list hundreds of examples in this book but one of my favorite is: Control the Options: Get Others to Play With the Cards You DealThis is a great tool which I use in pretty much every real estate transaction, I'm actually using it in a transaction I'm currently in!

IF I sold I would likely hold the money in hopes of things returning to a more level playing field for buyers.

@Rimon Swimmer If you want to play it safe, Whitehave, Westhave, Cordova.

Got a full ride scholarship to play ball and study.