A friend of mine has a single family home and first tried to rent it out at the peak time (also a college town, but she's on the outskirts) and there were so many other listings she ended up with a bad tenant just to get the place filled.

If you look at the US census data you will see that many cities saw their population peak decades ago.

Great thing about Maui, there really is no "off" season, there's a peak season during winter, but the rest of the year is great too.

It's like climbing a mountain over 10,000 feet; after you've been climbing for hours and hours, you're sure that what you see above is the peak, only to crest it and realize there is still a whole lot of mountain above yet to be conquered.

Sounds like you want everone here to congradulate you, but buying a brand new house in that price range that far out (where they are building lots of houses) at what is so far the height of the market in the peak season is IMO not cause for congrats.  

@Matt B. Yes

Whereas my own sfr near the beach has only taken a 20-25% hit since 2006, 1- and 2- bedroom condos in many areas throughout the county have depreciated more than 60% from the peak.

It makes sense that property taxes have fallen in the past five years with property values falling from the 2006-2007 peaks.

Almost related to a young couple that own a condo as a rental that is 60k underwater.The wife bought it when single as a primary residence at market peak with basically no down.

We had already blown open the entire main floor layout, with a header, large center island, and now we vaulted the adjacent living room ceiling to 20’ high at its peak.