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All Forum Posts by: Jason Eisert

Jason Eisert has started 5 posts and replied 30 times.

Post: Advice Needed: Selling a One-of-a-Kind Estate in Kailua Kona, Hawaii

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14

I’m reaching out to this group because I’m in a bit of a tough spot and could use some help. I own and manage an incredible property called the Kailua Kona Estate (you can find more details at www.kailuakonaestate.com). This home has been described by building department officials as the largest residential home on the Big Island, featuring an impressive 100-foot pool.

I purchased the property in 2021 when it was in a severely dilapidated state. The previous owners invested over $12M into building it between 2009-2012 but then left it vacant for years, allowing it to naturally age. Since acquiring it, I’ve fully renovated the property and transformed it into a successful short-term rental on 5 acres of land. Additionally, I own an adjacent parcel with 5 acres of coffee and have obtained permits to operate an agricultural tourism business there, with entitlements to build two more dwellings.

The estate is situated within a gated community, and while it’s a remarkable property with a lot of unique features, I’ve encountered some pushback from the neighbors, which has made me reconsider my position here. Despite my success with the property (we’re in the top 1% of homes on Airbnb), I’ve come to realize that it might be time to move on and sell.

In January 2022, after some initial renovations, the house was appraised at $9M, with the land likely valued at $1.2M. Since then, I’ve invested over $500,000 more into the property, so I believe the current value should be around $11-12M. However, given its design and commercial-like feel—originally built as a retreat center with a strong Japanese influence—I’m uncertain about the best market to target for a sale.

I’m hoping that someone in this group might have connections or advice on how to approach selling a property like this. I’m particularly interested in exploring international markets, given the unique characteristics of the home. As a realtor myself, I’m open to any referrals or suggestions on who might be interested in such a distinctive property. 

Thank you for any insights or help you can provide!

Post: Insurance is dropping me...

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Isi Nau:

Aloha Jason.  I'm interested in what KIN can do in Hawaii.  We recently purchased an apartment building on Oahu.  The previous owner was paying $3k a year with DB.  DB wouldn't write us a policy (for similar reasons mentioned in this thread).  I had three insurances agents hunting for: 1. a provider who would even consider writing a policy, and 2. a policy that wasn't sky high.  We only received a couple of quotes, and the cheapest one was $17k!!  I'm hoping to find a cheaper policy in the coming months.


 I’ll let you know what I find! 

Post: Insurance is dropping me...

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Michael Baum:

Insurance is crazy right now. Maybe forever. We have seen our policy rates double in the last couple of years. I am looking for other options.

Have you started calling around? Have you contacted the state insurance commissioner to see what is going on and how they can help?


 Just started looking. I'll have to reach out to insurance commissioner.

Post: Insurance is dropping me...

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Lisa Graesser:

This happened to us in Florida, no claims had been made. Company just claimed they were reducing their exposure in Fla. We had to do alot of shopping around and eventually found one. We now have KIN insurance,  not sure if they are available in Hawaii.


 I'll try reaching out to KIN insurance.

Post: Insurance is dropping me...

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14

Hello everyone! My insurance broker informed me that my insurance policy is being canceled, which is happening to many providers in Hawaii following the Lahaina fires. I have no claims on the insurance. I own a short-term rental property that operates much like a hotel, so I carry large commercial insurance. Has anyone else faced a similar situation? I would appreciate any advice on how to handle this, as well as recommendations for reliable insurance agents.

Thank you!

Post: Seeking Recommendations for Handling Handwritten-Look Mailers from Hawaii

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14

Aloha! I'm reaching out looking for suggestions on a unique challenge I'm facing with a direct mail campaign. I have a mailing list of over 3000 recipients and are aiming for a personal touch with letters that appear handwritten and are signed in ink. Ideally, we want the entire process to be managed locally to Hawaii to maintain authenticity and manage logistics effectively (stamps from Hawaii and not the mainland).

Unfortunately, I haven't found a local company on the Big Island that offers these services. If you know of any service providers who can write and prepare these letters, possibly on the mainland, and then ship them to me for a final local dispatch, I would greatly appreciate your recommendations. We are striving to avoid the appearance of the mailers being sent from the mainland, so any creative solutions or contacts in this realm would be incredibly valuable.

Thank you for any insights or contacts you could share. I look forward to your suggestions and hope we can find a suitable way to create a memorable experience for our recipients.

Post: Need Advice: How to Increase Bookings for Unique Luxury Hawaiian Mansion

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Luke Masaschi:

In all seriousness you look pretty packed... much more than properties in the area. Im not sure what you are looking for but have you used airdna to look at the areas average occupancies month to month compared to yours? I would assume you are most likely beating the market. The only way I see you getting more bookings would be marketing off airbnb on a direct booking website. Shoot me a message I can try and help as I beat my market in the slow months by staying 80% full but I use unique pricing strategy.

We do have a direct booking site really hard to compare our house to the market standard because we do not fit within the cookie cutter Airbnb that most of Airdna represents. 

it feels like we are in a completely different sector than any any Airbnb because of the uniqueness of the property. What I mean by that is it almost feels like Airbnb isn’t the platform we should be using to rent this place out. Some of that stems from the fact that there are no comparables but a lot of it stems from the fact that everyone from Airbnb that stays in our home says the home is insane and they are blown away and the pictures don’t do it justice. When I say that, all I hear is, I didn’t do a very good job at marketing the property and could have provided more value in the marketing and thus a higher price per night. 


Post: Need Advice: How to Increase Bookings for Unique Luxury Hawaiian Mansion

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Lauren Kormylo:
Quote from @Jason Eisert:
Quote from @Lauren Kormylo:

Jason, your house is amazing, I love it. 

I have a few suggestions for your listing.  Your cover photo shows the house all in shadow, and it's not showing its best.  Either lighten the photo, or change it to one where sun is shining on the pool area.  I agree with Jonathan about not quoting the remodeling price.  In fact, I would not say anything about remodeling and how you turned the property into beautiful space.  That sounds like it wasn't great before, and guests don't need to know that.  Just tout how wonderful it is, without alluding to its history. 

When you say "According to county records, our home is permitted as a five-bedroom dwelling", that sounds strange.  I would say, "the home has 5 bedrooms, with other spacious sleeping areas".    But your listing says and you have photos for 6 bedrooms.  Specify whether those flex areas have a door for privacy so they can function as a true bedroom or not.  And having a floor plan with bed and bathroom locations would be helpful to large groups, since many people will not be in the formal bedrooms.  And guests will want to see which rooms have en suite bathrooms.  

At the very end of the description, you say "This is a hosted rental."  Are you saying that you will be sleeping there too, or what does that mean?  Your heading says the guests are renting the entire villa. If you will be on the property, you should make that clear to guests. 

I priced some of your dates, and in Oct and Dec there are weeks that are $44,000 ! You are right that this will be harder to book, unless you can target the very wealthy. I have followed a guy named Bill Faeth for a few years now on his Facebook group and his YouTube channel. He focuses on luxury STR properties with loads of amenities as a way to stand above the crowd. He owns STRs and he co-hosts selective luxury properties for other owners too. You might look at his website, he also does coaching on targeting the luxury guest. I know he recommends having your own "landing page" for direct bookings, and using Facebook advertising among other things. I have used some of his tips, but I have not used his paid services so I can't personally recommend him, but his advice so far seems practical. https://www.billfaeth.com/



Lauren, thank you so much for your kind words and the valuable suggestions for our listing. I'll need to work on the cover photo. In fact, almost all the guests tell me "the photos dont do it justice" when they come stay in the home. It's very difficult to capture such a massive property. If you know any photographers that you recommend I'm open to suggestions!


 Also, I'll be removing mentions of the renovation costs and the property’s past condition. I like the suggestion. The logic makes sense. 

Regarding the bedroom count, I say "five bedrooms" because if I advertise 6 I am nervous that the county will come after me and shut me down for advertising more than what it's permitted as. The home was built with 7 bedrooms but they called them "Living Room" and "Lunch Room" despite obviously being bedrooms. However, I am not sure how I could creatively say that without crossing the line with the county. I'd be open to any suggestions you may have.

Thank you for your feedback!!! Look forward to your thoughts.


 If the county is going to take notice of your bedroom count, it will initially be to this heading on your listing "16+ guests, 6 bedrooms, 11 beds, 7.5 baths".  Since it says 6 bedrooms there, it will be searchable for that number of bedrooms by Airbnb's search function.  That's really where you want to stick to specifying 5 bedrooms if you don't want to get on the county's radar.  Then in the description, you can say "The house has 5 bedrooms, with 2 other spacious flex rooms that add  sleeping areas. These flex rooms are depicted in our photos as Flex Room 1 and Flex Room 2 with a king bed and three full beds respectively, and have doors for privacy." That way people know they can function like a true bedroom with a door, and they're not an open den.  It's just a tweak on what you already have written.


 This is great! Thank you so much for the advice :) 

Post: Need Advice: How to Increase Bookings for Unique Luxury Hawaiian Mansion

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Henry T.:

That's quite a property. I can't imagine it being booked  regularly with a one family limit. I'd market for small corporate events and porn film location. That's a party house!


 Playboy did stay here before I knew it wasn't allowed... lol 

Post: Need Advice: How to Increase Bookings for Unique Luxury Hawaiian Mansion

Jason EisertPosted
  • Rental Property Investor
  • Kailua-Kona, HI
  • Posts 31
  • Votes 14
Quote from @Bill B.:

Seller financing? Long term rental? Can you split it in to a duplex? Take a “break even” sale before interest, utilities, taxes, insurance eat you up? Talk to some “high end” realtors and see if they have opinions? Good luck. 

Ps. If you don’t mind me asking,  What is break even? Maybe you’d get an offer from one of the “more well-off” members of BP. Cut out the real estate commissions and it could help you succeed. Or a great BP realtor might have a buyer if they knew what you were asking. Like I said, good luck, you’ve got a toughie for sure. 

@Bill B.Here's the breakdown: 

Bought it for $4.95M

Early loan payoff is ~$175k ($5M @5% 30 yr fixed investor note)

Conveyance Taxes ~$90k

Improvements $1.6M ($400k done on lower property)...  as a note - I own 2 - 5 acre properties. One has this mansion, and a second ~2000 sqft house. The lower property is covered in coffee and has a newly built ~800 sqft shop / deck. Has the ability to build 2 homes on it. The original owner in 2012 spent over $11M building the properties and over $1M on landscaping/coffee orchards.

Misc Other Expenses Incurred: $250,000

Total: Around $7.2M. I have the property below as well that I would sell with it for $800k. Total $8M breakeven. 

We have appraisals from Jan 2022 for the mansion property ONLY at $8.7M and a second at $9M.