Aloha @Melissa U.
Just a few thoughts on your original post (plus a few assumptions):
-I think $92 a month for the vacancy rate is a little high. If managed right, you won't see a vacancy for 1-3 year. If you do, it'll be filled in 2 weeks. When the market adjusts it may take 4 weeks to fill.
-If the property is a condo, you may not have any additional insurance costs, depending on the building's policy coverage.
-Removing those two doesn't make a big difference in your bottom line, but it does help.
-With $60k, you should be able to find a unit that will at least break even each month.
A few general thoughts:
-A 20 year timeline/commitment to the Hawaii market can work out well for you. The key will be moving into bigger properties over the years, at key times, and into properties that meet specific criteria that fit your long-term strategic plan. It is completely possible to start with a condo and end up with a small (<10 units) apartment building in 20 years, or even less. It is possible to turn your $60k into close to $500k in that 20 years.
-Tax records are a good start at analyzing appreciation on Oahu, but are slightly lacking in accuracy and recency. But through MLS, it would be fairly easy to get exact appreciation rates for a specific building.
-I believe Oahu has 2 more years of steady price appreciation (about 10% cumulative). Beyond that, it's unclear. But historically, the market will likely adjust two years from now. For reference, in the last recession, prices declined 10%-20% depending on the area and property type. That's not annual, but cumulative. A price decrease is a price decrease, but compared to most of the country, that is pretty amazing.
-Who wins, cash flow or appreciation? I don't know. But what I do know, very very well, is how to make money in Hawaii's market. From a management and strategic perspective, turning $60k into $500k in Hawaii is not easy, but it's also not hard, with the right guidance.