As you sort of infer - we look at mitigating risk by how much security deposit we require.  

It may become not worth the effort, since you will likely need to run a dormer of some sort to get more head height.  

I would say that being within 15-20 minutes of town would be the max I would go if I were selecting a more secluded/private experience. 

You have to be very selective, and you need a long-term outlook to make sense a building in Chicago.

An attorney will help you work through other issues and matters, as there will be several that you guys need to sort out. 

We’re also considering purchasing another LTR near Disney to eventually enjoy with our newborn—a celebration of sorts for future family vacations.

I just sort of wing it.

There's lots of brands out there so user reviews would be bests to select but just know it may be more difficult to remove and some might have to be steamed and peeled off. 

Sort of looking at this as diversification of my portfolio.

Initially, I didn't select this route because I'm not located in the central part of Austin, but I would like to give this a try since the room is fully furnished, but will require some bedding, artwork, and a desk.