Where to start

Question

I have a few long term multi families but now I’m looking to venture out into STR. I’m looking at Benton harbor or neighboring Michigan coastal towns. Dows anyone have any advice or better places to start?

Renee Krystek · Answer

Congrats on expanding into STRs! Benton Harbor and the surrounding Michigan coastal towns definitely have potential, especially with their proximity to Chicago weekenders like me. I’d recommend digging into local tourism trends, seasonality, (as everyone above already mentioned) and how saturated the short-term rental market is in each area. South Haven and Saugatuck (was there last fall) are also worth a look as they tend to attract a lot of summer traffic.

If you’re planning to self-manage or work with a cohost, make sure to factor in setup and furnishing as you know first impressions matter a lot in this space.

Is there a reason you are drawn to this location? Are you nearby? I have a favorite real estate agent in eastern Michigan, Audrey Schultz. She owns STRs, is an agent, and a coach so if you want more local help she might be a good resource!

Michael Smythe · Answer

Check with RPOA organization

Drew Sygit · Answer

Your Network direclty impacts your Networth.

So, go meet other investors that can assist you in accelerating your learning curve.

Audrey Schultz · Answer

Hi Lane! I’m a blogger, investor, and agent specializing in STR. I’ve personally owned and managed a vacation rental with Lake Michigan frontage and would love to help you navigate the lakeshore markets. St. Joseph doesn’t allow STR but Benton Harbor does.

I go beyond supporting your property purchase and financing. I can coach you on how to set up your STR business for success and be there to help long after your transaction is closed. My contact info is on my website below, please reach out for a free consultation.

Audrey Schultz

ListWithAudrey.com

ModernFrontierswoman.com

eXp Realty | Legacy Group International

Collin Hays · Answer

A short term rental wlll work almost anywhere. Do you homework and scout out the competition on VRBO.

Andrew Steffens · Answer

I would state maybe the obvious that this is likely a pretty seasonal market.  I manage 95% in FL that is pretty busy all the time (albeit with some seasonality) but I also do some in coastal NJ.  I have one in NJ 2 blocks off beach that does $10k from Oct-Apr and then $100k May-Sept.  Budget wisely!

Anja Schaer · Answer

Wherever you’re looking, start by researching local STR rules, seasonality, and demand. Browse Airbnb and VRBO to see what’s already working in the area, what amenities are common, and where there might be gaps you could fill. Maybe try things out with 1 or 2 units first. And check the demand for Mid Term Rentals as well. Maybe that’s a better niche for your market. Good luck!

Alexander Zeisberg · Answer

Hey again — just wanted to jump back in with a few more thoughts now that the convo’s rolling.

On STR Rules and Grandfathering
Potential bans can definitely throw a wrench into things, but the good news is that most places have grandfathered in STRs that were operating legit and had the proper city approval in place.

That said, even those grandfathered properties need to keep up with changes in local rules as they come. And big heads-up: selling a property could mean losing the STR status — a lot of cities don’t let those rights transfer automatically.

There are also some quirky local policies around duplexes — like homes that weren’t registered before the rules changed now can't get a duplex permit at all. They won’t say it’s a “ban,” but they’re capping permits based on owner-occupied ratios and trying to “balance the community” or whatever. So... yeah, not easy to navigate without checking things case by case.

Where the Deals Are
A lot of people are focused on the stretch from Red Arrow Hwy west to the lake, and for good reason. It’s hot, and honestly, a lot of the properties are pricey — you’re talking $350K+ for a dated cottage on a small lot. But if you can update or add some value, there’s definitely profit potential.

Between Red Arrow and I-94/I-196, things cool off a little price-wise, but you still get solid beach access and some awesome pockets with charm.

Once you’re east of I-94/I-196, you’re in more rural/ag zones — lower prices, bigger lots, and way more flexibility on rules and zoning. Could be a great fit depending on your strategy.

One More Thing
Like @Renee Krystek mentioned — a lot of people forget how much it actually costs to furnish these places. Good furniture, good vibes, and nothing people can easily walk off with… it adds up quick. Definitely something to plan for.

If you're digging into this area and want to bounce ideas or need someone to help with the local stuff — zoning, permit status, whatever — feel free to reach out. Happy to help however I can.

Ghassan Jabali · Answer

Hello Lane,

I hope you're doing great. That is good to hear that you're venturing out into Short Term Rentals, particularly in Benton Harbor and Michigan Coastal Towns. I have family over in Michigan and it is always nice to see the lakes.

One thing I wanted to recommend when it comes to Short Term Renting is that if you haven't done so already to look at structuring with Trusts and/or LLCs for the renting, this can apply to your long term multi-family properties but especially with your STR properties for asset protection and anonymity for ownership interest. Having an operational LLC focus on the STR side, while separating it from the property ownership LLC can help create layers of asset protection.

Note: This information is for educational and informational purposes only and does not constitute legal, tax, financial, or investment advice. No attorney-client, fiduciary, or professional relationship is established through this communication.

Aaron Zimmerman · Answer

Following. I'd love to learn more about investing in the areas you mentioned. Love those areas. The main thing to be aware of is local laws and potentially banning STRs

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