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.

Purchased directly off the MLS using a cash (heloc) quick close offer and allowing the seller to live rent free for a couple months to assist her with the transition to her new home.

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.

The tenant are OK with this since they will get money returned if they leave the property in good condition.

I can call expired, vacant, lien, pre foreclosure, obtain timeline for selling (or listing if you’re a realtor), condition, motivation, price, and run comps (equivalent # of stories, .5 miles (not crossing major freeways), same # bedrooms, sq ft, whatever parameters you want set). 

The apartment we were moving into turned out to be in very bad condition.

Finally, I schedule a walk-through with the tenant during the first 7-10 days of ownership so I can document the condition with pictures, talk to the tenant about maintenance issues, or project improvements during the next turnover.

I will be notifying the property manager soon (according to our contract guidelines) that he will no longer be managing my properties-- he does not do any property inspections and does not manage the move out process well resulting in deterioration of my properties' condition and extra expenses and headaches for me .