I will mention that a hot tub could really increase the frequency of bookings. 

@Federico Dallo you mentioning vacation-type locations leads me to guess that you may want to use the property yourself occassionlly?

Now that you mentioned this, I looked into it and, at a glance, they offer "Full-Service Maintenance Coordination", which offers the phone answering, troubleshooting, etc.

I'm worried that i will purchase something based off burning a hole in my pocket and not for the sake of being a good investment (mentioned above already). 

Here's the deal: While searching on platforms like Zillow is helpful and anyone can do it like you mentioned, that's not why you need a solid agent.

Of the things you mentioned, seller finance is one to focus on if capital is low.

I was unaware of the tax-paying requirement you mentioned for adverse possession.

I agree with Erik, although their are some investors out there that will help fund the down payment/entry fees that you mention, they typically are friends and family that trust you and believe in you.

As I mentioned, it's a fine enough app, with enough logic and capability for small-scale acquisitions from the looks of it.

It's also really cold outside as well, which he mentioned that "we don't want anyone dying of exposure".