Would love to know your plan, my biggest problem is staying organized with all of this lol

The biggest pro being making a lot of money, but there are a ton of things to consider.

The property has documented annual rental revenue of $140,000. 

The biggest issue is that you'll be representing yourself, which means you are emotionally involved.

Biggest thing is going to be structural or foundational issues as long as that is solid it's okay.

If you have a hot dog stand and sell hot dogs and can prove revenue then a loan could be possible as you produce something.As an investor, you need a home that can produce something (income) to get a loan against that.

If a property has a low return on equity, as in low revenue relative to value, it would make more sense to sell because you likely have equity that could be redeployed elsewhere for a better return.

What this really means is:  VRBO is not meeting stockholders' demands for revenue and profit, so we're going to lower the nightly prices of our hosts' listings, so that we can meet those numbers. 

Oftentimes, a direct line to the owner is the biggest challenge.I'd be prepared to make an offer on the spot BUT I'd also be prepared to take things 1 step at a time.

Growing a roster is a great way to create predictable revenue too.