Haven't followed what slips are costing in Alawai but it's got to be the cheapest place to live in Waikiki discounting the boat cost. Get your name on the wait list for the boat lengths you might be buying
. My name came up in a year for a 40'-50' slip. Was very surprised at the short length of time on the list but might have been a fluke in timing. Was also on the list for a 35' slip but that was a 4 year wait before a slip became available. Turned down both slips as my free air travel had dried up and decided to leave the boat in Kona.
As far as the boat market in Hawaii, there have been a number of good deals on boats here but the market is thin. Hawaii is the start and quick end of too many round the world
cruises. So lightly used well equipped boats do turn up and the unavailability of slips makes local owner market slim so they languish and sellers get anxious.
As far as under the table slips, you have to get lucky as lease
agreements are out there but you have to be ready. I sailed over planning on taking advantage of the 4 month in a year provision on State Marina transient slips and hopefully finding something more permanent in the interim. Just happened to see an ad for a sublease in Honokohau on Craigs List the day after arriving. Had that for a year till the slip lessee found a boat of his dreams. Word got out I would be in need of a slip and I had a couple of people after me to work
out a lease agreement for their slip. Ended up bouncing around Honokohau for 5 years in 3 different slips before our name came up for a permanent slip. So there are ways to find a slip though live aboard may greatly increase the difficulty in keeping a slip. I was not a live aboard.
probably has a shorter wait list but it's not the greatest place to be. In the past there has been a lot of drug use and State seems to be dumping homeless in the area which don't do anything for the crime rate. Ko'olina has pricey slips in a resort environment
but think they discourage live aboard. There are also slips in Kaneohe Bay but most don't take live aboards.