@Taylor Daschyes, we used propstream with our own custom design. not handwritten but a high quality photo.

No, I highly doubt it.

Even though the nightly rate is high, the RE has such high value that the margins are fairly tight.  

I would find that to be pretty much not possible with a high volume listing agent.

The gap opening is roughly a 11 ft and 6 ft high.

You are a high w2 earner, The house is worth 110k today, you are buying from your grandma for 60k in exchange for free rent for life, upside ARV of 200k.The costs of owning the house will help provide tax relief on your high w2 earnings, you are buying a great chunk of equity that will pay off in the future, and you and your grandma are doing each other solids. 

In my experience, allowing these professionals to guide you can be highly beneficial, as they are likely to recommend properties they would be comfortable managing.

Or for the high-end primary homeowner has no legal way to 1031 exchange; so the deferred sales trust is a no brainer.

I've been a real estate investor my entire life, doing my first deal as a senior in high school ($5,000 mobile home).

These are prime locations, think near downtown or popular tourist destinations where demand for short-term rentals is typically high.