And lastly, I search FunishedFinder listings nearby, find comparable properties, and track the listed rent for a few months (does it increase, decrease?).

CRMs are just a tracking mechanism for how hard we want to work.

I am finding it a bit challenging to keep track of all the URLs like HOA, Electric, Gas, Solar, Taxes, etc. in one place. 

Hey @Brandon Schaar, reach out to @Darren Danowitz to help you get on the right track with assisting you and your wife to purchase your first house.

You're definitely on the right track and live in a great real estate market to be successful!  

You’re on the right track, but make sure to consult with your CPA to confirm your plan aligns with your situation.

In San Francisco, this choice is taken out of your hands and is instead a determination made from and by the Planning department.From an Investment POV, you are absolutely correct that combining the lower and the ground floor units is the best option to preserve your ability to perform a fast track condo conversion and generate the most equity in the shortest amount of time.

Question 1) does the depreciation recapture follow thru the 1032 exchange where you still keep track 50k worth of recapture?

My clients are using QBO and I just have to track all financials for them.I have clients that are mixed with Rental and Flips.It all depends if you expect a flip to last longer than 1 year, chances are you going to put them all in Balance Sheet Items. 

My opinion would be to serve a non-renewal as well after you track them down.