I have a listing coming on the market soon (less than 2 weeks) in Old Town Scottsdale walking distance from Fashion Square Mall, The District and Sprouts that will make the perfect STR and I want to be able to inform potential investor buyers of the legislation regarding vacation rentals in Arizona.My strategy is to market it as a potential STR as well as an owner-occupied for those who may want to house hack their high-end digs! 

Want to buy and hold in Western NY.

I disagree that there really isn't a "number", I believe most people that have 12-15 units and have a W2 job should likely have additional help in some fashion whether it's unskilled boots on the ground (friend, significant other), a PM company, or handyman you can call on.   

A lot of my clients have purchased in Little Village and the western side of Chicago in general, and it pretty much never makes sense to add a legal unit.

The most was probably 4-5 and they were taken in serial fashion, so one was denied before the next applied. 

Oak Island is where I'd like to go next as we have several STRs in Western NC, and would like to diversify and go towards coast now.ANy recommendation on real estate agent or your method for finding it?

I am excited that we got a sub-forum formed for the Western half of the state!

@John Knisely is a good resource for on market stuff and @Jimmy O'Connor is with New Western and gets some good off market deals.

The stark differences I have seen, especially coming from CA, the pressure to begin building in a more dense fashion just isn't prevalent like in CA.

With $15,000, it could be quite difficult to get into some of the western state's markets.