Quote from @Steve Englehart: I currently have two long term rentals and am looking into buying into the short term rental arena.  

With this in mind, if you intend to leverage short-term debt (hard money), it's even more vital that your underwriting is thorough and that you have the correct systems in place to tackle potential issues.

This property also launched my short-term rental journey, running our first Airbnb before transitioning it to a steady cash-flowing rental, allowing us to scale into bigger projects.

Mashvisor – Helps compare long-term vs. short-term rental potential, especially useful if you’re weighing both options. 4.

The short answer is No, you don't need it.

Short-term rentals of non-owner-occupied properties will also require a special use variance which is obtainable by starting with the completion of an application in the Zoning Department."

RW discovered that most clients shop with a "what are the monthly management fees" approach and not a "what are all of your revenue streams" approach.RW competes with a very competitive flat monthly management fee but then charges a minimum of 1 full month's rent for leasing and a host of other fees. 

https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

I do a combo of short-, mid-, and long term rentals on the northside of Chicago and surround suburbs.

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year.