Stop daydreaming about owning a vacation home. Have someone else pay for your investment.

Below are three questions you MUST say “Yes” to before considering investing in a vacation rental property.

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For the past ten years, my husband Shad and I have celebrated our anniversary with a kid-free weekend up in Bayfield (a quaint town on the coast of Lake Superior). After a four hour commute, dinner out Friday night, and a long walk to breakfast on Saturday morning… at around 1:40pm on Saturday we run out of things to say about the kids. We’d finally be forced to switch topics for the remaining 24-hours. This is when the magic happens.

We’d walk the streets of Bayfield chatting about life, goals, money, travel, books, the future … and us. We’d daydream about owning vacation property in the area and taking the girls kayaking through the Apostle Islands National Park. Ten years ago, my family owed over $81,000 in debt. So, we’d leave for the weekend and take our dreams home with us.

Bayfield - WIsconsin

It has been an interesting ride, with a variety of unexpected financial choices. This year we have no credit card debt and a third investment property in, you guessed it… Bayfield. We purchased a small rental cabin near the Apostle Island National Lake Shore.

Stay tuned for the story of our cabin, how much we paid, and how the finances work here. FYI–our little studio cottage rents out all summer, when we’re not using it, at $180 a night. Hot dog!

Our long term goal is to spend retired summers in Wisconsin and then head south for the winter. Sometimes when we pull into Brickyard Creek (which is where are cabin is located), I feel like I need to pinch myself. This is my life. This is our cabin. We own this.

Over the last year and a half, we’ve made wonderful family memories….


… We’ve also learned a lot about the ups and downs of owning a vacation rental property. We currently own two other duplex-rentals, but owning a cabin in the Brickyard Creek Community has been our first experience with a vacation home. There are many parallels and a few distinct considerations when considering purchasing a rental property.

Shad and I sat down and pulled together a list of 25 questions for couples to consider before investing in a rental property. However, before you dive into the details, you need to seriously discuss these three simple questions.

3 Questions You MUST Say “Yes” to Before Considering a Vacation Rental Property

1. Do you really want to commit to repeating ONE VACATION over and over again? Renting your vacation property releases some of the stress of feeling like you have to utilize the property all the time, yet you’re still making a strong time commitment to one specific area for many, many, many future vacations.

2. Are you ok with twice the amount of paperwork? Even if you’re using a property management company, you’re still going to need to keep track of insurance records, payments, tracking write-offs, taxes, and permit fees throughout the year.

3. Are you comfortable with strangers sleeping on your mattress? If you want to invest in a vacation home and rent it out, you need to be a-okay with unknown strangers sleeping in your bed. It sounds silly, but this is a big hurdle for a lot of people.

This last question can be a killer, BUT think about it… when you rent a hotel, condo or cabin with your family that bed has been used by a 101 strangers. Wouldn’t it be nice to have those same strangers paying down an investment property you own?

If you’re both able to answer YES to these three questions… then purchasing a vacation rental property might be a good fit for you too. Start off your chats with these simple questions and stay tuned for additional posts on owning a vacation rental property.


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