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I will probably start with about a 100K for a down payment on a condo or home when leaving the US mainland....
Should I work for a couple of years to save for a down payment on a more expensive place? My ideal house in kahala is about 2 million.
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Its tough to find a lender willing to go 5% down on a jumbo loan these days, even with flawless credit and solid debt/loan ratios. A year ago it would have been a piece o' cake.
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Any suggestions about where to live, whether to rent at first or buy , and whether I could really afford a home in a great area?
Where would you suggest living on a salary of about 350,000?.
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In addition to Waialae/Kahala areas, you might consider Kailua and, as someone else suggested, Hawaii Kai.
By renting, you can give yourself time to get a better feel for neighborhoods. The downside is the longer you wait, the greater the risk of even tighter restrictions and higher interest rates reducing your buying power further. (By the way, prices in the top areas of Oahu are, remarkably, still rising. There is no end of competition for those prize properties.)
If you are flexible and can imagine yourself living in something less than your dream $2M Kahala home, you could buy something a bit more modest in a solid area, grow some equity AND add to savings, and move up in 2 or 3 years.
If you do invest wisely now, you'll at least have your foot in the door. This is a fabulous market for buyers and investors!
If you're working from home, you will not have much difficulty with traffic regardless of where on the island you plant yourself. You learn to work your trips to town during off-peak hours. You learn to avoid Costco and the H-1 on Saturday mornings, too!