I am a real estate agent located in the City of Newburgh, which has grown over the past few years as a destination for many first-time investors like yourself.

A billionaire (founder of Pinnacle Vodka, can't remember name) has plowed enormous money into it, with the hopes of making it a "high end destination".

Imagine it like setting a destination on a map before starting a journey.

Orlando is a year round destination.

It is perfectly positioned for immediately generating income as a destination STR, since it has two houses on it (one being a large ADU).

We're looking to buy our first STR in Destin.

Also- because this STR is in a vacation destination we stay about 85% booked or more.

Google, McDonald's worldwide headquarters have moved here and a lot of tech & new start-up companies.https://www.businessinsider.com/most-influential-cities-in-the-world-2018-5#8-chicago-illinois-14https://www.americaninno.com/chicago/newsletters/chicago-just-jumped-in-a-ranking-of-tech-hubs-worldwide/Yes, property taxes are high, and, in the end, the tenants carry that burden, not the landlords.And let's not forget, Chicago is one of the top travel destinations in the World, so there is a lot of money to be made in AIRBNB if you like that route, plus as you actually moving in this town, as you are also going to live your life where you move - as a traveler, you'll appreciate a city that you'll totally enjoy with lots of public transportation, world quality art, architecture, music, sports, parks, restaurants, etc.https://www.chicagotribune.com/travel/ct-trav-chicago-rankings-20191231-20191226-azdidiyibrfu5h6wwyyntbq5c4-story.htmlGook luck to you!

Nearby Tybee Island is a popular STVR destination but they currently have a STVR moratorium. 

The proximity to popular destinations can make the units desirable for furnished mid-term rentals, which can yield higher rental rates.