New To Investment but looking to learn more about STR

Interior Decorator · Chicago, IL · Member since 2025 · 31 posts · 40 votes

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.

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Melissa HaworthBusiness Member

Real Estate Agent · The Panhandle | The Emerald Coast | Panama City Beach | Destin · Member since 2017 · 257 posts · 101 votes

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.

[email protected]469-658-2869

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Melissa JusticeBusiness Member
Rental Property Investor · Phoenix, AZ · Member since 2024 · 518 posts · 1k+ votes
1y
@Renee Krystek hey!
Before diving into suggestions, I'd encourage you to think about building a foundation of long-term rentals first. Why? Because long-term rentals give you predictable, stable cash flow, are easier to finance, and help you build the systems (like property management and financing relationships) that you'll need before jumping into the higher-risk, higher-reward short-term space. A strong LTR base helps you scale sustainably, even if an STR underperforms.

That said, there are still some great STR-friendly markets just outside the major hotspots. Here are a few to explore:

East Coast Markets Near Prime Vacation Areas:
Poconos, PA – Popular with Philly/NYC weekenders; more affordable than NJ shore towns.

Hudson Valley, NY – Not far from NYC but less expensive than the Hamptons.

Delaware Beaches (Rehoboth / Bethany) – Look at nearby inland towns like Millsboro or Dagsboro.

Outer Banks, NC – Look inland from the main strip—Jarvisburg, Powells Point, etc.

Western NC (Asheville area) – Very STR-friendly with strong tourism, hiking, and cabin demand.

Panhandle Florida (if you stretch "East Coast") – Look just outside of Destin or 30A for better prices.

If you're open to a hybrid strategy, like a turnkey long-term rental first to build equity and experience, followed by an STR later, it can make your portfolio more resilient and give you more leverage in the long run.

Happy to chat more about markets or help you weigh long-term vs. short-term strategies!
Best of luck,
Melissa
[email protected]313-221-8718
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Julio GonzalezPro Member
Specialist · West Palm Beach, FL · Member since 2008 · 4k+ posts · 1k+ votes
1y
Welcome to BiggerPockets, Renee! With your design background, you’ve already got a huge edge!

-Julio
561-253-6640
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Melissa HaworthBusiness Member
Real Estate Agent · The Panhandle | The Emerald Coast | Panama City Beach | Destin · Member since 2017 · 257 posts · 101 votes
1y
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.
[email protected]469-658-2869
2 Reply
Paul De Luca
Real Estate Agent · Chicago, IL · Member since 2018 · 1k+ posts · 1k+ votes
1y
@Renee Krystek
Welcome! You are correct Chicago does have some STR rules and regulations you should be aware of.
I don't own any STRs but I think the book Short Term Rental Long Term Wealth covers the topic well.
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Joseph Sauer
Member since 2021 · 46 posts · 57 votes
1y
Hey Renee!
Congrats on making the move into RE investing and looking into STRs!

I have one piece of advice, read Avery Carl's 2 books on STRs: Short Term Rental Wealth and Smarter Short Term Rentals.

Avery and her husband, Luke are the go to ppl for STRs! Very very knowledgeable, actionable advice in these books. Start here. It'll answer most of your questions as you get started.
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Jonathan KlemmBusiness Member
Moderator
Contractor · Chicago, IL · Member since 2016 · 4k+ posts · 2k+ votes
1y
Hello there @Renee Krystek! You've got a smart realtor - BiggerPockets is a great place to learn a ton and network with some amazing investors! Especially if you are here in Chicago!
I've been a short-term rental operator for a long time here in Chicago, and I can admit that it's gotten harder and harder to keep it up. Unless you are going to turn it into a business, I'd suggest long-term rentals because of the heavy lift of getting them going.
If you search the forums for Chicago AirBnB and short-term rentals, you will find a lot of old posts outlining some of the recent changes. Like having to have your ID state the address you are renting or use it for your homeowner exemption.
[email protected]
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Shea Murray
Chicago/Columbus · Member since 2022 · 49 posts · 50 votes
1y
Hey @Renee Krystek I don't disagree that the city of Chicago can be tough with short term, but I've heard some excellent success stories about short term rental in the Chicago suburbs.
Also, if you go the single family STR route, you can always pivot down into long term rental if it's not going the way you'd hoped!
I know a couple that owns, operates, and manages a bunch of STRs - here's a youtube video of them:
- I'd be happy to connect you with them! I'll send you a connection request now!
1 Reply
Micah White
Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
1y
Hi Renee!
Welcome to BP! You're in the right place to get all the information you need on taking that next step and investing in real estate. Happy to help answer any questions you may have!
Also, Chicago isn't the worst market for STR investing, as long as you know how to tackle it 😉
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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
1y
@Renee Krystek - welcome! It is Definitely not easy to do short term rentals in Chicago. There's no sugarcoating it. However, it's not impossible!

Once you figure out your market and buy a property, there can be some significant tax advantages. Just make sure to rent the property for 7 days or less, find a way to materially participate by working in the business and tracking others hours, not hiring a property manager, and not using it too Much for your personal enjoyment. With 100% bonus depreciation being back, it can be highly lucrative. That said, make sure the STR is a good investment for you
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Mike FisherBusiness Member
New Lenox, IL · Member since 2024 · 103 posts · 57 votes
1y

Hey @Renee Krystek,

Love that you’re jumping into real estate investing—and with your background in design, you’re already ahead of the game. Being able to furnish and prep a space with the right eye for detail is a huge asset, especially in the short-term rental world.

You’re right—Chicago can be tricky for STRs with all the city restrictions and evolving regulations. But there are still opportunities in certain neighborhoods and surrounding suburbs, if you know where to look. Expanding your search is smart too—lots of investors are doing well in smaller, less-regulated markets with steady tourism or travel demand.

I’m based in Illinois and wear a few hats in this space—licensed builder, realtor, property manager, and investor—so I’ve had a front-row seat to what works (and what doesn’t), especially for new investors. Happy to share insights or help you think through markets, numbers, or setups if you ever want to bounce ideas around.

Feel free to reach out any time. Excited to see where this journey takes you!

[email protected]
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Micah White
Real Estate Coach · Chicago, IL · Member since 2020 · 171 posts · 64 votes
1y
Hey! It’s awesome you’re bringing your arts and interior design skills into real estate—that’s a huge advantage when it comes to staging and creating appealing spaces. You’re right that Chicago’s short-term rental market is pretty tricky due to regulations and competition, so being open to other markets is smart.

When it comes to finding the right areas, whether for long-term rentals or STRs, the key is to look for places with strong rental demand, steady appreciation, and local regulations that support your strategy. Many investors I know explore markets in the Southeast, Texas, and smaller metros where STRs are booming and regulations are more favorable.

If you want, I’d be happy to share some of the markets I’ve seen perform well, plus tips on how to research neighborhood fundamentals and vet properties beyond just aesthetics. Also, combining your design eye with solid market knowledge will make your investment really stand out.

Feel free to reach out anytime to swap ideas or ask questions!
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