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All Forum Posts by: Melissa Wesling

Melissa Wesling has started 3 posts and replied 134 times.

Post: Short term rental

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97

Hi Julia!  I have short-term rentals and my husband and I self-manage them from out of state. You mentioned short-term rentals in "resorts".  Are you specifically looking at properties that are part of resorts?  

Post: New Investor from Holland MI

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97

Hi Mac!  I invest in short-term vacation rentals in southwest MI if you want to connect!  We love visiting Holland when we are up that way.  

Post: vacation rentals and why they are better

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97


I have both LTRs and STRs and agree with the information given above. Reach out if you'd like to discuss further.
Many times if an investor wants to purchase a short-term rental property in a vacation market, their goal is to earn income, but also have a property for their own use in a place they would like to visit and/or build equity on a property they would like to retire in someday.  

When wondering if a short-term vacation rental is a good investment for you,  first decide if any of these items meet your investment goals:  

  • Is it your dream to own a property in a vacation destination?
  • Are you seeking a particular return on your investment?
  • Do you want to diversify your portfolio with a home that will appreciate in value?
  • Are you looking for an investment vehicle that offers tax advantages?

Guests typically look for properties in close proximity to the beach.  However, if you are not on the beach a property with other great features can make up for it.  In FL, a pool is a must and a south facing lot seems preferred for more sunlight.  As mentioned above, be sure to research the rental regulations in the areas you are looking.  Hire an experienced realtor who is knowledgeable in their vacation rental market to help you search in a rental friendly area to find the right property for your investment goals.  I am happy to connect if you have more questions about the FL markets! 

Post: Help on finding my second property

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97

@Saul Clavijo Hi! I own and manage both STRs and LTRs. Both of my LTRs are attached homes and part of an HOA. As mentioned above, when you are looking at these properties, be sure to check with the HOA on their regulations for renting. Many only allow a certain percentage of the homes to rent, some require that the owner live there first before renting it (with some exceptions such as if it is a family member who will be renting). Also one of the cities requires a license and inspection annually, so that is something to look at as well. The positive to an HOA is that they do take care of the exterior maintenance, lawn, snow, etc. so you don't have to worry about that piece. LTRs are less time consuming to manage (as long as your tenants are good), but I still think STRs have potential for more profit.

Post: Best Place/State to Invest on Rental Properties

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97

@Sridhar Yedupati The best place to invest in depends on your investment goals. If you are looking for a good return, a recent study done by Rented, Inc. rated the FL panhandle for best ROI. There are definitely some other hot markets right now but demand is high and supply is low, so investors often have to be ready to make a quick decision in the hot markets. It is difficult to determine which state is the best because it is a case by case basis depending on the market, individual property, and the owner. Once you narrow down the market, be sure to hire an experienced realtor that is knowledgeable about the regulations in their vacation rental market so that you can find the right property in a rental friendly neighborhood. I'm happy to answer any specific questions if you'd like to connect!

@Vera B. We are in South Haven, but Saugatuck, St. Joe, and New Buffalo are also popular markets.  There are rental ordinances in place in these areas, so be sure to have a realtor in the area that is knowledgeable of those rental regulations to guide you to the right property.  Let me know if you'd like a recommendation!  

Ok so I will say Mark has some really good points, however I am a Midwest girl investing in the Midwest because it is familiar and drivable and we took family trips there when I was growing up.  @Vera B. is there a personal reason you have your eye on northern Michigan (family there, visit often, etc.)?  

I will say that northern Michigan has done pretty well with rentals post-Covid.  I have friends investing up there in Harbor Springs, which was recently voted in a study as one of the top 25 places to buy a vacation home based on home sales and vacation rental performance data.  Traverse City is also a very popular spot for vacation rentals. Golf, ski, woods, lake, and outdoor activities draw people to northern MI.  Heading south, we looked at investing in Holland, it's a great area with the state park, Dutch village, and tulip festivals.  2 reasons we didn't invest there:  the beach and downtown area are not near each other and we wanted to be closer to the Chicago area.  We settled a little further south with our STRs in southwest Michigan.  The rentals in SW MI have had high occupancy as people working and schooling remotely have taken more "flexcations" away from the cities. Happy to connect if you have any questions about SW MI or STRs in general!

Post: Bank Accounts for STR’s? What do you do?

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97

My husband and I have 2 LLC's, one for our short-term rentals and one for our long-term rentals. The STR LLC is named after our STR brand and the LTR LLC has a separate name, again as a "brand". We use xero for our accounting software. I'm not an accountant or attorney, but just wanted to share since there were some questions about it :)

Post: Short term rental resources

Melissa WeslingPosted
  • Investor
  • Chicago, IL
  • Posts 148
  • Votes 97

Great advice above.  I self-manage from out of state and don't have much to add!  When you are looking for a property, hire an experienced agent that is knowledgeable about vacation rental investment properties in their area. They can guide you to the right property that has rental friendly regulations. Also be sure to think of your new property as a business and not your home.  Using smart home technology and property management software helps things run easier.  

What markets are you looking at?