New To Investment but looking to learn more about STR

[Renee Krystek]

Hello All,

I am new the property investment world so my realtor recommended I come here to learn more. I have a background in arts and interior design so I understand how to furnish and get a property ready to list, but I have no clue on how to start finding the right areas and everything else that goes into it. Chicago is NOT the best market for STR so I am open to learning more about the rest of the US and peoples experiences elsewhere.

[Melissa Haworth]

Hey, welcome to the world of property investing—glad you’re here.

It’s awesome that you’ve got a background in arts and interior design. Honestly, that puts you ahead of the game when it comes to furnishing and staging a short-term rental. A well-designed space makes a huge difference, not just for photos but for guest experience and reviews.

You’re right—Chicago isn’t exactly the easiest market for STRs these days. A lot of investors are looking to other parts of the country with fewer restrictions and stronger vacation demand. Florida, especially the Panhandle (think Destin and Panama City Beach), has been a hot spot for exactly those reasons.

What makes these areas appealing:

• Steady tourist traffic all year
• More affordable than other coastal markets
• Regulations that are generally investor-friendly
• Plenty of local property management options if you’re not planning to self-manage

Since you already know how to create a beautiful space, the next step is learning how to run the numbers and identify areas where STRs actually perform well. I always suggest looking at things like local regulations, seasonal occupancy trends, and what kind of returns people are getting in a specific neighborhood—not just the city overall.

Happy to share more about what’s working in my market if that’s helpful. You’ve got a great foundation already—it’s just about pairing your skills with the right location and strategy.