I'm looking at a property with two buildings.The first house is very well kept and reflects its fair market value - no substantial room for improvement there.

Otherwise your head will spin with options and cause you to do nothing.

@Mike Rodriguez make sure your tax returns show substantial income from your rental and Airbnb activity for at least two years before quitting the W2 or you may have a hard time qualifying or bank financing.

I can see where it might be worth while when interest rates are 6-7% and the HELOC is substantially lower....but at the rates they are now I personally don't see much of a point...the benefit of the leveraged debt being so cheap now is to be able to earn more on your money elsewhere.   

Any shifts away from the Fed’s current outlook, he added, “will place more upward pressure on mortgage rates.”Grocery Store Properties Thrive During Pandemic.

I wanted to go head and introduce myself. 

I pay state income tax in CO on the rental income and state tax in CA for my W2 job.However, I sold some stock (which was held for years) in 2019 and noticed a slight increase in my CO state income tax.Then in 2020 I sold substantially more stock and my CO state income tax payment doubled.

If you are looking for a more appreciation play building on the baxter side would be substantially more desirable. 

Cashflow doesn't exist without substantial down payments.

You just need to run the scenario through your head and figure out what would the actions/reactions be.