But when all the record indicate something different than the actual physical condition you need to figure out why.

I just see it like a co-signer on a residential loan, just different term (maybe even slightly different conditions since it’s non-residential).  

@J Hurwitz, what is condition of property?  

@David Lee Hall, III Yea mine is in similar condition.

We knew no one else could see the potential given its cosmetic condition, and since it had been on and off the market so many times, we negotiated the price down $60,000 from list, and they fixed $10,000 of damage before we closed.

It was in “good condition” meaning it didn’t need a renovation.

And remember, a tenant already living there is not going to be as demanding for newer/nicer things than a potential tenant when it turns, so without knowing the condition and cost to upgrade is a very big risk.

There is another cabin in that same resort community that is comparable in terms of condition and is slightly larger renting for about $100 per night on average.What questions should I be asking myself?   

I can't speak to condition of a house, but I typically assume over a long term, you will need to reserve $400+ per month.  

It really depends on what you are looking for......the higher the ROI on paper the higher is the risk that it will not materialize and on the other hand the lower the ROI the more stability you can expect in terms of quality of tenant and condition of the property.