This would be my first foray into real estate investing... and I absolutely 100% agree that the best move is to establish a track record using my own money and conventional loans before considering using private money.

It's a lot of work upfront but once the team and systems are established it gets easier and as you get better you can expand to another city. 

Establishing a separate entity, such as an LLC, for your rental property business could provide more flexibility in claiming deductions associated with business-related assets like vehicles.

Did you get a few months of the home's utilities just to establish a baseline of what the cap should be? 

Like @Bruce Woodruff said you have to establish your goals and "why" REI or homeownership should be in your life.

I'm a very analytical person who won't start a new venture without first gaining a solid understanding, establishing the right framework and connections, and ensuring that I'm securing a great deal.

That's a lot to ask of a complete stranger!

It establishes a base that's $40 lower, which all future rent increases are based on. 

I could see fully comping 1-2 nights at low season rates, particularly if one doesn't have a lot of reviews yet, but would you, as an established host with tons of reviews, comp a full week or more of a prime season stay? 

In more established markets like Austin or Omaha.. from what I’ve heard in Bloomberg, guests value transparency as much as good rates.