Hello Brian,You'll need to perform some calculations for this task.

Making connections in the community may lead to business opportunities and offer insightful information about the local market.Look into internet platforms where properties could be listed in addition to more conventional approaches.

The property will perform as a medium term rental if short term regulations expand to the area.

Which in turn will bring plenty of other investors and general business to the market.

You can make money at all of them but you want to go into your real estate investing Business fully understanding the impact of each strategy. 

Even then you need a business license if you are collecting any kind of payment for it even if it is your place.  

Both were customers, ran small business, and held money with the bank.

.- Bullish on long term appreciation as many high net worth individuals move to the area, surrounding areas seeing luxury development, and businesses (Wall Street South).- Majority mom and pop operators, easy to become a top listing with the right marketing and property!

@Will Boller, in a quick click around on Interval International's website (https://www.intervalworld.com/web/my/home) a major exchange for timeshare properties, it seems like it is 50/50 from my small sample looking at properties in the northeast USA, with a handful allowing Sunday weekly check-ins too.Granted, this exchange is not an Airbnb, but it is all weekly stays in condos run, presumably, by large professional operators that have studied this business to maximize revenue.  

It is always more difficult to end business relationships with friends and family but you can't treat these working relationships any differently.