The roof was in good shape and the roofer kept complaining there was nothing wrong.

Nothing wrong with the traditional 20% down method on a property and rent it out, provided you can recoup your money back in a reasonable time.  

When I try and do any extensive research for properties none of them even come to close to making financial sense or am I just looking at the wrong type of properties (SFH).

Tax value is often wrong. 

As a contractor myself I was excited to see this as a resource, when I saw homeadvisor I was pretty upset.Homeadvisor preys on contractors, sells them bogus leads or over used leads, locks them into incredibly high prices which dont get me wrong if your getting quality leads you pay but there leads are literally wild goose chases.This is so prevalent they filed a class action lawsuit against them.Please do not use home advisor, shop and vet you local contractors.

Nothing wrong with either method.  

We started out not doing instant booking and switched because we might be doing something wrong in confirming reservations since no one was following through and booking. 

Is it the wrong time of season?

Hi Ron, I got some details wrong and tried to edit the above but couldn't figure it out... so I created a new entry.  

You just have to live in the house for a year (someone correct me if I am wrong) before you can move out and utilize it as an investment property (house hack).