All good input. IMHO the 265 is the best looking Grady out there (any of the express models for that matter) but the deal killer for us was the lack of recessed walk-around decks, and lack of a dinette table and seating below. The center helm is great, and the cockpit is fantastic.
Tuna - there are two 265's locally, Bristol Yachts in San Pedro has one, the seller is in Chino. I think he wants too much for the boat because it has OX66's on it, but it's on a trailer. You could always negotiate the price if you decided you really want one. They were low hours, but we all know they're stinkers and gas hogs. Seems to me it was mid 70's.
The other one is owned by a fellow named Walt, he's been on the forum here in the past, his boat is in ABL and he's in San Diego. We went down to see his boat, it's very nice. Has HPDI's but with quite a few hours, around 900 or so. Boat is well equipped and well taken care of. He's had it advertised for a couple of years, I think he's mid 50's which is really a decent deal for what it is. It's slipped, so no trailer. BTW, I have a local source for aluminum trailers if that need comes up.
And I think there's a late Sailfish in Newport, you'll have to scour the internet ads. It was pretty new for quite a chunk of change, 90's I think, maybe more. And there was an '04 Sail in SD, but that was last year and it's probably sold by now.
There is also a nice Islander just north of San Francisco, you'll find his ad in usedboats.com. Young pair of HPDI150's on that one, and a trailer. Good price too, in the 50's. I've heard it said here the Islander is a 'skinny sailfish'. However no aft berth on that one.
Frankly, if you're going to keep the boat on the trailer (as I was thinking as well, but may have a slip coming up) I would lean toward an Islander. They were designed for towing, the bigger boats not so much but can be done with the right truck. Caltrans permit is $100 a year, virtually zero restrictions, you just have to have the permit and flags and signs.
Let me know if you need help finding boats for sale. If I can get a buyer on my 208 will be trying to deal on a Sailfish (1st choice) or an Islander (2nd), with at least HPDI's or the intention to repower with Etecs or Zooks.
Boats cost a little more on the left coast, I think it's a combination of shipping costs and demand. There are some real deals on the east coast, and lots to choose from. There's always the possibility of a fly out, buy, and have trucked. I figure about $5500 to do that. And I'll bet there are some forum members that would be willing to preview something for a fellow grady-guy to make sure it was worth pursuing.
EDIT: 'cuz i can't spell for $Hlt!