-Will it be robust enough to track additional business expenses that are NOT tied to a single property (IE; Business insurance, Home office, ETC?)

I currently live in a 1000 sqft home that we pay a mortgage on.

I am a lifelong San Diegan, and I have house hacked every home I have ever lived in. 

I am worried for two reasons: removing the garage will reduce the value of the homes more than the extra unit will add, and the property value will not increase that much with the extra unit(s).

If we price the home based on what they thought they could get for it, it will sit for weeks/months.

Although most of my stays are <7 days, I've had a few longer stays (business travelers and a family that was going through a full home remodel).

My wife is a Top25 Realtor in Ft Wayne, I'm a licensed contractor and home inspector.

https://www.donotcall.gov/report.html I am getting so many text messages, both political parties as well as from people wanting to buy my home...

However, let’s go with the scenario that you rent and HELOC the Las Cruces home.  

And a handful with 25 to 50 homes.. same thing I fund the front end of the BRRR and they refi and pay me off.My latest adventure is funding land flippers and I have two that are knocking it out of the park..