Also, I am also looking for contracts as well.

@Kaleb GarrettHave you confirmed with zoning this can be done?

I intend to add a closet to the den and make it a 3 bedroom adding value as well as remodel the entire unit.

Mechanicals, roofs etc. can be towards the end of their useful life and pass inspection but then the cap ex can't be absorbed in many of these C/D neighborhoods.

I highly recommend investing in a property management software, such as Hospitable, for syncing your calendar, automating messaging, and scheduling cleans, as well as a dynamic pricing tool, such as PriceLabs, for optimizing your pricing based on market demand, local events, and seasonality. 

If you ever leave them it will be deleted, so be sure you are backing it up! 

So you will not be owner occupying a primary residence.

Many investors fall into this "do-it-all" trap, believing no one else can handle things as well as they can.

I think one thing that is helpful, is to be more directed in your question and what you're looking for with regard to coaching.

In retrospect, the answer has to be sheer overconfidence!