If it's a place you and family would enjoy and can pay for itself then it's worth probably going for it assuming there are no hidden liabilities you have yet to uncover. 

One thing led to another, we are now uncovering that the mold/mildew build-up is substantial and has spread to the adjacent closet. 

The long way is to just dig into the country records database and you will eventually uncover the owner names and addresses (if not owner occupied). 

So it cost you a few hundred bucks to move forward with confidence – then you start making money.Best Case SituationYou uncover some real warts on this frog.

This time is spent uncovering what we can about the seller.They are motivated but what is motivating them to sell, once we get to the true motivation we try to structure a deal that gets a fair price (for them and us) and solves the problem we can then capitalize on their motivation. 

There is going to be much more information uncovered as you dig in.

We mostly want it to pay for itself and hopefully make a small profit until we can retire and use it as a summer retirement home.As far as income and vacancy projections, a quick internet search uncovered 2 other similar cottages nearby with availability calendars and price rates for the next year.

What questions can we ask them to uncover any red flags?

What questions can we ask them to uncover any red flags?

I came into this deal thinking it was going to be a base hit, but with all these uncovered issues, it's starting to look like it will be an ongoing headache / cash killer and not what I had originally planned.