It's best to ask the owner for references of previous guests who have stayed with them in the past. I always like to ask the age of the property? how long they have been renting? Is there a management company that they deal with and if so, which one so you can call them as well.
If your looking at Rentalo you can usually see how long they have been on rentalo. If it's been a couple of years you can assume they have not had any issues as they can and are still listing thier property.
Just use good judgement and ask anything you care to know. The owners will anwser any questions you may have. They are used to it since there are always a lot of first time renters.