All Forum Posts by: Christopher Jordan

Thanks for that info @Jason Eisert  From my cursory reading of the summary it seems that TARs in resort-zoned areas will still be allowed. Everywhere else will be limited for investors but still available for a resident wanting to rent out part of their home or an Ohana unit. 

For investors in resort-owned areas this would seem to be a beneficial thing as it will limit STRs to those areas only, likely driving up prices. What are your thoughts?

 @Kelly O'Keefe Great insights. I sold half of my business and am looking to offset my taxable income for this year. I will still collect a W2 from the business (I'm still an employee) as well as K1 for a percentage of profit. But most of my income in 2024 will come from the business sale. If the business sale proceeds or K1 are considered passive income, can the strategy as described here with my wife (no W2 income) as the active manager of an out of state STR property, work to offset the business sale proceeds?

@Bryan Vukelich I love Kailua area but STRs seem pretty limited there and unless I’m mistaken there seems to be a big push in Hawaii to limit STRs outside of resort zoned areas.  

 Thank you @Julio Gonzalez

Thank you Bryan for the clarification on local contact vs management, you've helped to keep the dream alive.  It's good to know that its still possible to self-manage and thus qualify as an active business for tax purposes.  

To be honest I've always dreamed of a second home in Hawaii and STR is kind of an afterthought and nice way to cover some of the mortgage expense. But if I could actually cashflow and be profitable, I'd certainly be willing to entertain other areas of Hawaii. I'm not really a Waikiki guy and wouldn't necessarily choose to stay there often, but if I could find a 2 bedroom condo at that price that cashflows...I'd certainly be interested in looking a little closer.

Hello Bigger Pockets, I'm a newbie. I just sold my business and in looking for ways to offset capital gains taxes stumbled across a strategy in which a STR can write off all depreciation in year one via a cost segregation analysis, thereby reducing taxable income greatly for a specific year. Owning a vacation property in Hawaii has been a lifelong dream of mine, and it seems that this dream may also be able to generate some tax savings for me.

I'm looking for a 2 bedroom or more condo in a resort-zoned area of Hawaii, specifically the Waikoloa Beach or Mauna Lani Resort areas which are already resort-zoned. I know that Hawaii is trying to reign in STRs so I don't want to stray outside of a resort-zoned area, however this means that costs are inflated. There are very few condo units selling sub $1M, and I really don't want to spend much more than that.

Hawaii is a year-round rental area, so shooting for 80-90% occupancy seems do-able. I don't really expect the property to cash flow, I realize that it's an expensive place to operate a STR and that on-island management is necessary by Hawaii law, but I'd like to be able to cover most of my mortgage and expenses after putting 30-40% down.

Does anyone have experience in this market, or with this cost-segregation to write off income technique? Hawaii law requires an on-island manager, but in order to qualify as an active business I’ll need 100 hours managing the property so hiring a regional manager may hurt my tax write off plans. Any thoughts on how to abide by Hawaii rules AND  utilize this to offset capital gains?

Hello Bigger Pockets, I'm a newbie. I just sold my business and in looking for ways to offset capital gains taxes stumbled across a strategy in which a STR can write off all depreciation in year one via a cost segregation analysis, thereby reducing taxable income greatly for a specific year. Owning a vacation property in Hawaii has been a lifelong dream of mine, and it seems that this dream may also be able to generate some tax savings for me.

I'm looking for a 2 bedroom or more condo in a resort-zoned area of Hawaii, specifically the Waikoloa Beach or Mauna Lani Resort areas which are already resort-zoned.  I know that Hawaii is trying to reign in STRs so I don't want to stray outside of a resort-zoned area, however this means that costs are inflated.  There are very few condo units selling sub $1M, and I really don't want to spend much more than that.

Hawaii is a year-round rental area, so shooting for 80-90% occupancy seems do-able. I don't really expect the property to cash flow, I realize that it's an expensive place to operate a STR and that on-island management is necessary by Hawaii law, but I'd like to be able to cover most of my mortgage and expenses after putting 30-40% down.

I'm looking for references and advice for finding lenders, property managers, etc. in the competitive Big Island Hawaii STR market. Thanks!