Think about the policies and communications around the classic boy/girl friend and unauthorized person lease terms and procedures (from on-boarding through screening and lease signing).....But if it is really too stressful, look at your scale (is duplex or ten-plex right for you and your work/life balance), your market (the neighborhood --working class or upper class), your team (like a good eviction lawyer or contractor) and see if it is a good fit...

If it is not zoned for multifamily and the city has no plans to update that subdivision, you may want to chalk this up to an educational expense.

Right now it seems the board members are doing most the work.

And the owner is paying you not only to enforce common sense rules, but to understand the ADA and the proper & legal way to hande a request for a reasonable accommodation.Most city and county governments have a position called an ADA Liaison (or something to that effect) whose position exists to train local businesses and landlords on ADA requests and what is reasonable / unreasonable as it pertains to accommodations (often the same person that gives training once or twice a year at the local Board of Realtors, so you might even be able to reach out to them for a point of contact).Rather than operating in a vacuum, or taking your advice from a public forum, why not reach out to that person in your jurisdiction and get an opinion straight from the horse's mouth?

Implement themed experiences like a "Movie Night" with popcorn and streaming access or a "Game Night" with popular board games.

Will new board members/president or secretary be selected from the new condo owners?

I am a total Newb to this board guys so feel free to yell at me if I can do things different for the benefit of the community :)I want to use this as a space to chronical my journey and stay connected with folks in the industry so yeah.

It's people-intensive and blends the amenities of an airbnb  with a boarding room/inn concept.  

I once attended a free Kiosaki seminar on buying in the stock market........then they asked us all to play Roberts stock market board game to aquaint  us on the basics...

However all my dealings have been above board and have never taken advantage of anyone like this.