Is you angle to accommodate families more with a 4 br?

If the property would be difficult to fill at the market rate, then go ahead and continue bending over backwards to accommodate this tenant.

The STR which I am contemplating to switch is in a big ski town & does cash flow well.. trying to max it up & not worry about rising expenses in maintainence , read the other day about traveling nurses needing individual rooms & with a huge dearth in inventory for longer term accommodation - there possibly could be a more steadier & higher income stream 

Before she moved in, she did not ask us about any accommodation, her room is small so cannot fit a desk (she brought her own TV stand for her TV in the room).

You definitely want to go into it without name dropping airbnb right from the get go as it can have some negative connotation right off the bat, but what you want to focus on is positioning yourself as a company that focuses on accommodating short term guests under your management, assuring them you have the right rental insurance in place, cleaners, handyman (may be optional in their building) that will keep that specific unit in the condition in all of the building because that is a must in order for you to operate your business successfully.

And so far have been able to keep it booked back-to-back (sometimes even negotiating with guests to accommodate early move in-move out).

Over accommodating up front may set the wrong expectations for the remainder of the lease.  

I would recommend Oz Accommodations. http://www.aplacelikehome.com/I myself am a local investment property lender, but I am actually interested personally in acquiring some smaller multifamily in Overland Park.  

They have been great tenants and we want to accommodate them while they search for a house to buy, etc.Thanks for any feedback! 

But those tend to be higher quality properties with a full suite of amenities to accommodate families.