We have a small cabin that has lots of reviews that ranks high, but we have some larger homes that are more expensive and dont book as consistently as our small cabin. 

With that said, here are some questions I would ask myself about the situation: Historically, have the students paid enough in the 9 months to cover all the expenses associated with these properties?

Why do you have 24k in cleaning fees as expenses for an STR?

I learned about the power of leverage with real estate investments and now make 16k/month net after all expenses off rentals by doing a cash out refi on my primary residence to get me in the game.

On the other hand, passive strategy will buy more expensive house at a nicer neighborhood.

You make revenue here and there but the goal is to generate enough in the winter to sustain all the expenses for the entire year. 

Or they can be sold to investors.I think they are particularly attractive for new investors to buy as a house hack - you live in one and rent out 3, most, if not all, your expenses will be covered.Look at what it last sold for, has it appreciated?

Part of my calculations does figure in vacancy, repairs, and capital expenses.  

I have about $400K to deploy, but would prefer to buy several duplexes rather than 1 more expensive building.

It's been difficult to find deals that pencil with heightened interest rates and expenses.