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All Forum Posts by: Jason Eisert

Jason Eisert has started 5 posts and replied 30 times.

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 @Jonathan Greene:

You are hamstrung by the community this is in. I reviewed your listing and you are targeting families which is a hard target for this big of a property. It certainly has appeal for family reunions and multiple families together, but you are almost telling them not to book. The listing description is very rigid (see below):

"This home is meant for families looking to create beautiful memories. With such a unique experience comes a responsibility to respect the land, home, and neighborhood. We love our community and the atmosphere we have cultivated for this newly renovated home. As such, there are strict requirements that Hawaii State Law Quiet Hours must be observed outside the home past 9:30 PM (feel free to go snuggle up with some popcorn in the 16-seater movie room!). We ask that groups who book are limited to one family. The pool, pickleball court, and lanai close at 10 PM each night for your safety and to observe quiet hours. This home can't be used for parties or events."

What one family is coming to use 11 beds and 7.5 baths? You either chose the wrong place to try to do this or you are overly restricting who can come. You basically sound like an overlord in your listing as if someone is going to get in trouble as a guest if they sneeze past 10 pm and that is not enticing at a high price tag like this to have to be careful.

The property looks great, but your description starts with telling them that you spent 1.2m in renovations. No one cares about that. Tell a story, but you can't tell it like this being so restrictive of who comes there.

@Jonathan Greene Thank you for your feedback. Your insights are indeed eye-opening, and I appreciate your straightforwardness. You're correct about the potential misalignment in my listing's target audience and its tone. The section stating, 'This home is meant for families...' was directly influenced by local regulations. Hawaii County operates as a "complaint-driven" county, so they don't enforce any rules unless someone complains. After a neighbor's complaint on my property, the county scrutinized my listing and told me that all Airbnb's on the island have to abide by a strict 'one family' rental rule. Something that nobody follows and transparently feels like they selectively enforced on me... About a year later, when I was in a meeting with the Planning Director, he mentioned this rule is unenforceable because any guest can say they are "family", and how do I verify that? This has placed me in a challenging position, as my competitors are not being held to the same standard due to lack of complaints against them. 

I don’t explicitly ask guests if they are family upon arrival. From my observations alone, it sometimes seems that not all groups who have stayed here fit the 'family' definition, but this has never caused any issues. Especially considering that we are in Hawaii where "everyone is Ohana". 

Originally, the property was designed as a retreat center, but it didn't receive the necessary planning approvals for broader use beyond a single family residence. 

I’m going to rework the description to better reflect this and to make it more inviting and less restrictive. Any further suggestions on how to navigate these regulatory challenges while appealing to a broader audience would be greatly appreciated. How have others in similar situations managed to balance such constraints? As a note... there are properties on the island that are "luxury" but per building department officials my house is the largest residential house on the big island with the biggest residential pool. 

Post: First time STR in Hawaii to offset capital gains?

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

As far as supply and demand, once many of the rentals shut down (if the county actually enforces the bill) then yes there would be more demand for all STRs. That being said, the resort areas are already permitted for rentals. Thus, this new bill is only going to introduce additional hoops to jump through AND it creates a way for neighbors to take away your permit. 

For example, if your renters are making noise that any neighbor considers to be a "disturbance" (literally that's the word they use in the bill), the police will be called and if there are 3 verified disturbances, you will loose your ability to rent the STR for 2 years.


This is a bit of an extreme example.. but it is one of many that could take away your ability to rent. 

Post: First time STR in Hawaii to offset capital gains?

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

@Christopher Jordan I live in Kona on the Big Island. I'm heavily involved in the new bills being written to impose additional regulations on the islands STR's (now TAR's). Would love to connect and chat. Happy to answer any of your questions. To help you begin though, the most recent drafts of the bills can be found here: https://www.hawaiicountytar.com/

The Leeward Planning Commission will hear the proposed bills on Thursday, April 18 @ 2 PM (streamed over youtube on Hawaii Planning Department's site). Following the hearing, the Windward and Leeward PC's will make recommendations and it will go back to council for amendments and readings. Still have months before it will be turned into law.

@Carson McGee lets connect as well. Always love to meet like-minded people in the same area! 

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

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

I am the owner of a 10,000 sqft luxury mansion in Hawaii that I have spent the past two years renovating and managing. We've found that the property is perfect for large families, yoga retreats, and corporate groups. Despite offering almost every amenity for an ideal vacation, my efforts to increase bookings through more than ten non-exclusive agreements with local property managers and continuous outreach to travel agents have not been fruitful. You can view the listing here: https://www.airbnb.com/rooms/739311990337556133.

I am seeking advice on more effective marketing strategies to enhance visibility and drive bookings for this unique place... It's got a large cost per night and our target demographic isn't "cookie cutter" like most listings. If anyone has insights, experiences, or can recommend specific platforms or techniques beneficial for marketing unique luxury vacation rentals, your guidance would be highly appreciated.

Thank you for sharing your expertise!

Post: Looking for Utah Wholesalers and Local Skilled RE Investors

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

@Will Fraser Someone I could potentially volunteer to work with to gain knowledge from or someone who love to discuss deals and expand their network.

Post: Looking for Utah Wholesalers and Local Skilled RE Investors

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

@Simeon Miller Anyone you may know that could be interested?

Post: Looking for Utah Wholesalers and Local Skilled RE Investors

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

@Simeon Miller I'm still young and ignorant to a lot of things in real estate. Although I have experience rehabbing and doing contracting work, I only own one duplex south of a college campus and didn't do a major rehab on it.

Seeking to work with someone who has that experience and track record that could analyze the deals I find and give me feedback / partner with on deals. Of course I'll make it worth your time too if I partner. Looking for someone who wants to build wealth together quicker.

Post: Looking for Utah Wholesalers and Local Skilled RE Investors

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

Hey @Will Fraser! Thanks for reaching out. Starting when I was 13 a neighbor of mine introduced me to Real Estate. He owns over 150 single family homes and is often experiencing turnover and buying / selling deals. Because of this, he reached out to me to help him fix up places that tenants wrecked between turnover and rehab new deals that he purchased.

Sometimes he would contract things out (like a new roof, major plumbing issues etc.) but for the most part, me and him (and sometimes my brother) would always fix it all up. This experience also taught me who some of the best contractors are in Utah County / Salt Lake County also.

Post: Looking for Utah Wholesalers and Local Skilled RE Investors

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

Looking for someone with experience 'BRRRRing' in Utah that could give me advice and in turn I'll add value to you by sending you deals and offering my time to help out to build your portfolio.

I've got about $150k sitting in the bank and access to ~$500k from summer sales and my businesses. Hoping to do a BRRRR in Utah that I can manage the rehab on. I've got experience working and fixing up over 100 deals.

Post: What would you do with 70k cash during Covid?

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

Educate yourself more on the BRRRR method and do that. That way you can increase the velocity of your money.