However, I'm hesitant because the rent wouldn't cover the new mortgage, putting me net negative monthly.

Use a reputable expert like @Dave Foster and you’ll be covered.

Hello everyone, I purchased my home two years ago, and currently, I have a tenant renting a room for $800, which helps cover my mortgage.

One thing I'm trying to do is to test different cover photos to see which ones draw a greater % of click-thrus (which seems like a reasonable thing to test).I'd like to be able to view the Airbnb stats to see, for each cover photo I test, things like what % of people click through on it.

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?

You may want to look at concessions to help cover costs or buy down your rate to a comfortable payment. 

Are you trying to afford a house much more expensive than your W2s could cover? 

There is also parking per unit and impervious cover that could be an issue.

The buyer would need to show solid financials also of course (good credit, experience operating rentals, proof of funds for down payment and adequate reserves to cover any unexpected cap ex).

However, every insurance company has no idea what I'm talking about and don't seem to cover this.