Building indoors, even if it is a small space, can be easily accomplished with an unskilled, less expensive workforce when they are given 3D work instructions on monitors or tablets similar to the drawings provided when assembling a cabinet from IKEA.

While I generally want to keep the long-term tenants it seems that the one who smokes heavily indoors is also going to be the biggest handful overall and so it is a toss-up on how much I really want to keep her there. 

@Bob HardmanAgreed with the other comments on here; I will add that townhouse style get much more interest than up/down.

The management companies seem to charge a lot for airbnb style properties, do you see this being worth it?  

We've thought of all the indoor aspects (beds, seating, kitchenware, etc.) but parking is one that was not at the top of my mind. 

Then you need to compare location - traffic, neighbors, use, and style...

They are decorated like Hugh Hefner's mansion.New for 2021, all houses now have indoor plumbing and an outdoor cat*.

Is this how I get a seat at the table, Wall-Street style?

Ohana (mother-in-law style) studio units are extremely common and it is common practice to live in the main house and rent the ohana (short or long term).  

In Washington state N of Seattle the install is very typically $2/sq ft. the price of the product is what you decide for quality and style.