If something was to happen it will help you sleep at night knowing your property won't burn a hole in your pocket if you had to get someone in with a lease.  

Property is about $800,000 and looks like daily rate in summer is about $500 a night.

Any economic Pros out there can dive a little deeper on this subject so I am able to explain this better to my Clients?

Am I willing to drive there at night?

However, I am also not being greedy about it; neither have I been thinking of switching to the construction business because that is a completely different business model and there is also an inherent risk lurking in diving into a new business model you have no experience in.

Tenant A (night owls living in 1st floor) has been reaching out to us because she has seizures and had been getting multiple injuries due to Tenant B's "slamming and banging in anger"  as he has a baby (probably tenant A makes noises at night).

@Logan Fullmer Tobyhanna is proposing to make 10 guests max and 7 nights minimum 

I've been diving into the due-diligence on the NE housing/rental market and I am starting to get a lay of the land, but I would love to hear from anyone with more experienced in this particular area on any major 'gotchas' to be on the lookout for as I'm dialing in my search. 

My hope in diving into real-estate investing is that I can shape my life in a way that I am able to pursue these passions for more than a couple weeks a year. 

For close in neighborhood demographics, go to a few of the local Grocery stores and sit in the parking lot Friday night after dark, Saturday morning, and Sunday afternoon.Look at the people, and how they are dressed, look at their cars and trucks--guess their income level.