The upside is if it was your primary the first $500k would be tax free Definitely talk to a tax guy BEFORE you do anything.

A HELOC or cash-out refinance is definitely worth exploring if you want to free up capital for more investments, but make sure it fits your goals and comfort level.

I personally focus more on appreciation, but if I wanted more cash flow I would definitely go to a fringe area and buy a new build rather than going to an older area and buying a cheaper property.

I would definitely reach out to @Raymond J.

If not from the person in office, then definitely from the person running against them.

Responding quickly, like you do, definitely makes guests feel valued and reassured.I think the choice between automation and personal interaction depends a lot on the host's availability and scale.

Definitely sounds like an interesting asset class.

I told him I definitely wanted to go that route. 

And you can definitely pay off your home faster if you focus on running all of your expenses through it and watch your expenses. 

That may be the path for a year or two while you figure this out.