Keep in mind each state is different also and NY has some specific regulations in different industries. 

Is anyone familiar with the City of South Euclid regulations on rental property?

Local Landlord/Tenant laws and applicable Real Estate laws concerning rental transactions and required licensing and handling of Client funds; Federal Fair Housing; Fair Credit Reporting Act; applicable EPA regulations; HUD rules for certain projects financed with HUD money and of course Title IX subsidized housing issues; OSHA rules for employees (office AND maintenance workers); Licensing and Insurance requirements required/recommended for contractors that you hire; IRS rules related to employees and income reporting for your Clients and vendors; accounting "best practices" for Client funds; business insurance and record keeping requirements for your locale and type of business entity, and probably a few others.

@Michael ClarkI'd have a conversation with your loan officer on that, and how strict they are going to be.  

Many municipalities regulate STRs.

That is a tricky situation but you could implement stricter tenant screening processes, implement strict rules and consequences for tenants who violate the terms of their lease, try to work with the owners of the surrounding properties to address the issue of problematic tenants, offer incentives for good tenants such as rent discounts or referral bonuses, and consider partnering with local organizations or community groups to improve the area and make it more attractive to potential tenants.

my personal take:fix and flips only make sense in an appreciation marketlike in CA when the interest rate is low and the market is stable.buy and hold only makes sense in an appreciation marketfor cashflow it makes sense to invest in a cash flow market only (midwest)STR only makes sense in the place where you want to have a vacation there and in a heavily regulated area.So for me, it's not about the house, it's about the market situation and location-specific. 

Also differentiate yourself from all the other vacation rental houses by offering great amenities such as Jacuzzi, proximity the beach, etc.There are lots of regulations and rules depending on where you are looking for vacation rentals in South Florida.

The origins of one year really come from three revenue case rulings where the judges issued their rulings by stating a time period that was appropriate (but as you know it would have been only strictly applicable for that case). 

This gives you another way out if your Airbnb doesn’t work or you have regulations come up that prevent you from continuing to do short term rentals.