I'm trying to help you be comfortable with what you buy BEFORE you pull the trigger.

Great job recognizing an opportunity to do creative finance and reaching out to the community for help.My recommendation to figuring out what to offer is by simply talking to the owner and asking him what he needs to support his family and be comfortable.

They have gotten so comfortable with us that sometimes we have to ask them to please bill us for stuff they should have invoiced weeks or months ago.

The more property you inspect, the more of an expert you will become in your area.Once you feel comfortable with inspecting properties, learning the right questions to ask, understanding your local market, and HOW to evaluate each potential deal, THEN you will know a good opportunity when you stumble upon it.You can transfer those skills into looking at other markets and will have some clues as to what makes a good deal.

One could very comfortably go 50% leverage for example.     

Whether it's for business trips or family vacations, our rentals are designed to provide unparalleled comfort, luxury, and convenience.

I've also seen hosts post of a photo with the direct booking URL on a sign, although I personally would not be comfortable doing that. 

A knowledgeable realtor should be comfortable discussing these concepts and applying them to potential properties.Ask about their network of contractors, property managers, lenders, and other professionals who can assist with your investment.Taking the time to find a REALTOR with the right experience and expertise will help ensure that you make informed and profitable investment decisions.

Get out of your comfort zone.

As for when to call in a contractor, it really depends on the scope of work and your comfort level with DIY projects.