Some info that would be helpful to know would be the value of the house and outstanding mortgage amount.Yeah, I’ve been trying to rent out the other room, but I’m not sure how to market it without the hassle of having two different roommates.

I don't buy from assignors for two main reasons...liability and fictitious numbers. 

This year two more moved out and now we are down to 5. 

To @Dmitriy Fomichenko and everyone please disregard/ignore what I wrote above;  I was tired and got two different things confused.  

Below that is a parlor floor, which has the highest ceiling in the building and this floor is connected to the ground floor via an interior staircase which we added doors to both ends to break up the lower duplex into two separate living areas.  

That is, buy one home in city X (where I don't live), live in it a couple of months let it be an STR the rest of the time and then the next year (or in two years) repeat again in the same city. 

Hawaii is one of the two markets I operate in (and Anchorage, AK).

Omaha, Chicago, Austin, Phoenix, even San Antonio-I’m always keen to chat and share what I’ve learned from two decades of navigating the twists and turns of this world.

We are looking to capture a rental or two and one of those possibly being another STR. 

I have stories for a book or two.