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Episode 066. Buying a House & Moving: Tips from Maui Realtor Jessica Baker

Episode 066

Many families are moving this year out of want and/or need. If this is you and you’re considering selling, buying, renting, or relocating…or if you just want to hear some interesting and wild real estate stories, this episode is for you!

Jessica Baker is here with us today to give some practical tips for buying and selling a home, things to keep in mind for local and long-distance moves, and even Hawaii and Maui specific suggestions and stories. Jessica is a Maui based realtor with Hawaii Life and a personal friend who has been a knowledgeable and kind resource for me and many other families here on the island and is definitely someone I want to share with you.

Moves are stressful and complicated…our hope is that this conversation gives you some insider ideas, peace of mind, inspiration, and encouragement.

Jessica’s Bio (in her own words):
My journey to Maui began at a very early age! Well before I could read I always wanted to look at picture books of tropical fish and marine life. Eventually I would share with anyone who would listen, “When I grow up, I am going to swim with dolphins in Hawaii!” This was a very big dream for a kid in Michigan.

Fast forward to 2006. After graduating summa cum laude from the University of Michigan, I was fortunate enough to take my first (and only) vacation here to Maui with my parents. While we were having dinner that first night at the iconic Pioneer Inn in Lahaina Town, I just knew that the island was calling me. Armed with two suitcases and a bicycle, my next flight back to Maui two months later was as a brand new resident.

Now I have happily lived in Lahaina for fourteen years. As a child my parents couldn’t keep me out of the water – I would spend as much time as possible in the chilly waters of Lake Superior – and I was a competitive swimmer in high school. Surfing was a natural progression, as well as snorkeling and open water swimming. I’ve completed both the Maui Channel Swim and the Waikiki Roughwater Swim. When I’m not in the ocean, I also enjoy hiking around the island, yoga, baking, reading a good book, and spending time with my husband and our dog Lucy.

I began my professional career here on Maui in Fine Art Sales then transitioned into Real Estate at the end of 2011. It was another natural progression based on my evolving interests and education. That first year I was awarded the Prudential Iwado Realty Rookie of The Year and worked almost exclusively in Commercial Sales & Leasing. Several years later I have now sold commercial properties – and even more single-family homes and condos – all across the island from Napili to Wailea, Wailuku to Kula, even Hana!

My mission is to help my clients achieve their goals – whether they’re buying or selling – when the timing is right. I am strongly committed to providing clear, consistent communications and building long-term relationships, and have the diverse sales experience to back it up. I have been consistently ranked in the top 20% of Maui Realtors since 2015. Top 9% of Maui Realtors in 2018. I am a member of the Realtors Association of Maui Board of Directors and hold the position of Director-At-Large. I’m also a member of the Maui Commercial Roundtable and Co-Chair of the Realtors Association of Maui Technology Committee.

Oh! And did I ever swim with dolphins? Sure did. December 2007 was the first time of many. Life goal achieved. I love my Hawaii Life!

In this episode, Jessica & I talk about:

  • Long distance vs. local moves
  • How we both came to Maui
  • What to look for when looking for a realtor
  • Questions to ask your realtor
  • Healthy boundaries & clear communication
  • Clarifying expectations with your realtor
  • When to schedule the moving company
  • Things families have done really well to help kids get settled
  • The benefits of seeing a house without kids in tow
  • The importance of seeing “how the house will live”
  • Moving tips: labeling boxes,
  • Moving from the mainland to Hawaii
  • Long term rental tips
  • Prepping your kids for the move
  • A bit about how kids process the transition
  • Asking for help during a move
  • Over-planning and under-planning
  • Moving resources (being local and location specific)
  • Box #1…and what it should have in it
  • If your dream is to move to Maui…what’s it’s really like
  • WILD stories about moving and showings!

Jessica’s Links: Website, Instagram, Facebook, YouTube, Zillow and Blog

Change of Address Click to Download
Moving Day Essentials Click to Download

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Primally Pure: Thanks for Primally Pure for supporting today’s episode. Primally Pure, is one of my favorite companies. They excel at creating safe, natural skin care products made with quality ingredients. Primally Pure has extended their line to create products for the home. Their new Palo Santo Aromatherapy Collection is awesome! They’re also the makers of my favorite all-natural (& effective!) deodorant. (I love their blue tansy one). They’ve generously offered a discount code for listeners: be sure to use the code: LORIBETH10 for 10% OFF your first order. For my personal review of their products, head over to

Homeschool Explained: Today’s episode is sponsored by Homeschool Explained, an online course I created to help parents begin their homeschool journey with confidence. I was getting a lot of questions from parents about my family’s homeschool journey…they wanted to know more but weren’t sure where to get started or if it was a good fit for their family. So I started teaching in-person workshops here on Maui to help parents sort that out. But then requests starting come in from other islands and other places asking if I could put it online from them, too…so I did! I totally get it, starting any new journey can be overwhelming…especially when you feel this call on your heart to homeschool but aren’t sure where to begin. That’s why I’ve put over 10 years of homeschool experience and insights into this easy to follow, easy to use online course that answers common questions, helps you work through worries, and saves you time.

Homeschool Explained is for anyone who is interested in homeschool (now or in the future) but isn’t sure where to start. The information in this course will help you make an educated decision about whether homeschool is the right fit for your family and help you understand what modern homeschool days actually look like—all while covering major topics like curriculum, homeschool styles, subjects to teach, cost, state laws, socialization and so much more. This course takes the guess work out of where and how to begin and leaves you with solid support and resources. Start your homeschool journey with confidence! Find out more at


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