Either they don't have the knowledge of the additional paperwork required, or just have bad taste in their mouths about Sec 8 altogether. 

Think a boutique style coffee shop, a restaurant, tasting room etc..

Better IMO to err on the side of making them feel like they got treated "more than fairly" to set them on a course towards a third year of renting than to save $50 now, leave a bad taste in their mouth over the laundry issue, and turn the apartment over next year.

I got a taste of my first STR property in 2018 and have always been looking for ways to scale the Airbnb model.

I don't even live in the building so I thought this sounded too risky for my taste.

These types of things leave a bad taste in peoples mouths. 

@Rendy RichiezWhen you absolutely, positively, need it so bad you can taste it!

Posting that information here is in bad taste however.  

If you plan to build, do it tastefully and make sure your neighborhood association knows what you're doing.

My general rule of thumb is being out of state, I would rather your first deal in Milwaukee be a single / double in terms of return, but it gets you comfortable with the market and your core team (Agent, PM Company, GC's), and most importantly, it leaves you with a good taste of investing here.