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Old 10-16-2018, 08:04 AM   #21
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When you are ready to travel, give me a call. I will house sit for you for free. I will even do your windows!!! Mahalo.
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Old 10-16-2018, 02:47 PM   #22
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Which island?
I'm on Oahu now, and want to eventually land on Maui or Hawaii Island (if the VOG stays low).
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Old 10-16-2018, 03:00 PM   #23
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I'm on Oahu now, and want to eventually land on Maui or Hawaii Island (if the VOG stays low).
I’ve heard from one of my masssage therapists from the Big Island, her kid has to travel to Honolulu for some serious medical treatment. Are you sure you want to do that when you get older?
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Old 10-16-2018, 03:06 PM   #24
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I’ve heard from one of my masssage therapists from the Big Island, her kid has to travel to Honolulu for some serious medical treatment. Are you sure you want to do that when you get older?
The diving is so much better on Hawaii Island than Oahu, I do want to live there until diving is less important (maybe from 55 to 70), then I'll consider moving to an upscale Waikiki apartment close to shopping and dining.
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Old 10-16-2018, 03:11 PM   #25
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The diving is so much better on Hawaii Island than Oahu, I do want to live there until diving is less important (maybe from 55 to 70), then I'll consider moving to an upscale Waikiki apartment close to shopping and dining.
I agree, snorkeling was better at the Big Island then anywhere else.
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Old 10-16-2018, 03:13 PM   #26
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I’ve heard from one of my masssage therapists from the Big Island, her kid has to travel to Honolulu for some serious medical treatment. Are you sure you want to do that when you get older?
I was on the Big Island a few weeks ago, and was explaining to my friend that I seriously considered moving there instead of Honolulu, but I was concerned about the lack of stuff to do there. Now as I'm closing in on 60 I'd worry about the medical care. The whole traumatic experience of getting my elder mom to a hospital on Maui several years ago was eye-opening on the problem of medical care on the neighbor islands
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Old 10-16-2018, 03:17 PM   #27
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If it is 3 years or less, I would park the money in safe funds, CD's or short term bonds. Yes, the housing market can go up but it can also stall or go down. For that short of a term, I would avoid stock market risk. I also would not want to be a long distance landlord. Sounds like fun. Enjoy your travels.
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Old 10-16-2018, 03:38 PM   #28
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The diving is so much better on Hawaii Island than Oahu, I do want to live there until diving is less important (maybe from 55 to 70), then I'll consider moving to an upscale Waikiki apartment close to shopping and dining.

Can't argue with that. I scuba dived and snorkeled a lot my first almost 10 year in Oahu, but every time, I went to the Big Island, I had pangs of regret.
It's so much nicer. If you are in 40s or early 50s and good health, go for it.
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Old 10-16-2018, 10:09 PM   #29
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If you rented and had a property manager find/screen tenants and look after the property while you travel, could you be cash flow positive? If so, I’d rent it and reassess when you return. We sold our So CA rental when we lived in the Northeast and really regretted that later.
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Old 10-17-2018, 12:05 PM   #30
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If you rented and had a property manager find/screen tenants and look after the property while you travel, could you be cash flow positive? If so, I’d rent it and reassess when you return. We sold our So CA rental when we lived in the Northeast and really regretted that later.
Yes, we'd be cash flow positive, by a bit. I like the idea of keeping it, only because we'd have a place to come back to when the overseas travel stint is done; however, it's not in the best neighborhood, or where I really want to be in retirement. It's convenient to the freeway, malls, shopping, and downtown Honolulu, but it's a noisy neighborhood.
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Old 10-17-2018, 12:09 PM   #31
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Yes, we'd be cash flow positive, by a bit. I like the idea of keeping it, only because we'd have a place to come back to when the overseas travel stint is done; however, it's not in the best neighborhood, or where I really want to be in retirement. It's convenient to the freeway, malls, shopping, and downtown Honolulu, but it's a noisy neighborhood.
If you don’t like the location I’d let it go. This is obviously a very personal taste type decision and not purely financial.
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Old 10-17-2018, 06:26 PM   #32
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If you don’t like the location I’d let it go. This is obviously a very personal taste type decision and not purely financial.


The problem is that if you get out of the HI real estate market, travel for 2 years, and buy another property, you may have to pay a lot more than you think. At least if you keep your property while traveling, you can sell after you return and buy something at current value (whether up or down).

When we sold our So CA property, one year later we paid $245K more than the selling price of our former property for a place a few blocks from our previous place, 500 sq ft smaller. Values had really appreciated and had we already retired, we may not have been able to buy an acceptable place in So CA. I’m guessing that could happen in Hawaii too, but don’t know.
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Old 10-17-2018, 07:06 PM   #33
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The problem is that if you get out of the HI real estate market, travel for 2 years, and buy another property, you may have to pay a lot more than you think.
...bingo! That is the crux of the dilemma!
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Old 10-17-2018, 07:20 PM   #34
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The problem is that if you get out of the HI real estate market, travel for 2 years, and buy another property, you may have to pay a lot more than you think. At least if you keep your property while traveling, you can sell after you return and buy something at current value (whether up or down).

When we sold our So CA property, one year later we paid $245K more than the selling price of our former property for a place a few blocks from our previous place, 500 sq ft smaller. Values had really appreciated and had we already retired, we may not have been able to buy an acceptable place in So CA. I’m guessing that could happen in Hawaii too, but don’t know.
When was this? Honolulu has a lot of high rise condos, not the same in SoCal. Again real estate is very local. 20 minutes from me, house prices don’t go up in lockstep with my area. Know your area is key.
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Old 10-17-2018, 07:59 PM   #35
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The problem is that if you get out of the HI real estate market, travel for 2 years, and buy another property, you may have to pay a lot more than you think. At least if you keep your property while traveling, you can sell after you return and buy something at current value (whether up or down).

When we sold our So CA property, one year later we paid $245K more than the selling price of our former property for a place a few blocks from our previous place, 500 sq ft smaller. Values had really appreciated and had we already retired, we may not have been able to buy an acceptable place in So CA. I’m guessing that could happen in Hawaii too, but don’t know.
You just don't know what the real estate markets will do in the next two years, nor how much money you'll spend holding onto an unused place or dealing with renting a condo and losing the capital gains exemption for several years.

If you were definitely planning to return to the same area that's one thing. But if you are not, as the OP states......

We sold a house in 2005. Traveled for 5 years. Meanwhile big real estate market crash. Even got a tax credit for buying another house 5 years later - in a different city.

Obviously we lucked out on the timing.

Interest rates are rising. Prices might come down due to that pressure. It's just impossible to know.
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Old 10-17-2018, 11:10 PM   #36
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You just don't know what the real estate markets will do in the next two years, nor how much money you'll spend holding onto an unused place or dealing with renting a condo and losing the capital gains exemption for several years.

If you were definitely planning to return to the same area that's one thing. But if you are not, as the OP states......

We sold a house in 2005. Traveled for 5 years. Meanwhile big real estate market crash. Even got a tax credit for buying another house 5 years later - in a different city.

Obviously we lucked out on the timing.

Interest rates are rising. Prices might come down due to that pressure. It's just impossible to know.


I agree - totally unpredictable. I thought the OP said he wanted to return to Hawaii after traveling. I could be wrong, but was thinking that even if he wants to relocate within Hawaii, keeping a Hawaii property would make that much easier. If the market crashes, he won’t get as much for his place but a new place would have also gone down in value. If the market continues to accelerate, he may need that appreciation to afford a comparable place in another Hawaii vacation.

I would feel differently if the OP would have significant negative cash flow by renting, but he says it would likely make money net of costs.

Either way it’s a risk, OP. For me, I would think about the worst case - if you sell your property now and invest the cash in something relatively safe and property appreciates 40%, will you be ok with that? If you keep the property and the market crashes, will the market likely be down also for the new Hawaii location you want to relocate to?

No crystal ball here but DH and I decided we will never sell our So CA property unless we are committed to never living in the So CA again. Been there, done that and it cost us over $250K.
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Old 10-18-2018, 08:04 AM   #37
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Thanks! I've been following the Hawaii markets...days on market are increasing a little, and I've noticed an uptick in price reductions recently on Hawaii Island. However, the addition of luxury condos has moved the median and average prices up. In some luxury markets, interest rates don't matter, as buyers tend to buy with cash. Kona real estate has been through many cycles. I think what may be different this time is the number of baby boomer retirees moving into the area. Thanks!

I would hold onto it. Kona is a world-travel destination. Rent it out and bank the write-offs to offset any tax concerns. Do that until you no longer find it appealing to make those mainland-island flights anymore.



That's what I would do. I know when I moved to Maui, my only regret was not holding onto the home I sold to move there. Hindsight is 20/20.
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Old 10-18-2018, 08:26 AM   #38
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I'm thinking about traveling around the world also, but my wife is reluctant to sell our house. If we sell, we will not come back to the same place.
Insurance and taxes will be about $11,000 a year. House is about $620,000, probably will get us $550,000 after the cost of selling.
If I do sell, I will put in a 50/50 portfolio.
50/50 of what and what?
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Old 10-18-2018, 08:35 AM   #39
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I would hold onto it. Kona is a world-travel destination. Rent it out and bank the write-offs to offset any tax concerns. Do that until you no longer find it appealing to make those mainland-island flights anymore.



That's what I would do. I know when I moved to Maui, my only regret was not holding onto the home I sold to move there. Hindsight is 20/20.
I believe his condo is in Honolulu hence the screen name HNL Bill, he wants to buy in Kona eventually.
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Old 10-18-2018, 08:36 AM   #40
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I believe his condo is in Honolulu hence the screen name HNL Bill, he wants to buy in Kona eventually.



Whoopsie! Even better! Honolulu is an international hub. No problems keeping that rented!
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