Aquasport had a long history of building good solid boats with progressive features but have been out of production for close to 10 years so you won't get that "legendary" GW customer service.
2000 is the last year for the 272 as it changed to a 282 in 2001 (with no changes to the hull - just changes in the cabin area). That is Greenwood for sure so I don't think you have to worry about the wood in a 2000.
Having said that, I took a look at the Aquasport 275 in the video below and have to say I like some of the features (assuming they are both hardtops with similar power)
http://www.youtube.com/watch?v=SLbjDuXKyYo
First off, the swim ladder is on the same side as the transom door which makes a lot of sense. On the Sailfish, you have to walk across the transom stepping over the outboard cables. Not a major problem but a minor annoyance.
The 275 baitwell is located forward near the passenger seat, rather then on the port side of the transom. The baitwell on the Sailfish can get in the way when your fighting fish near the back corner of the boat.
Also, the 275 has a folding transom chair that retracts for fishing - this feature didn't appear until later on the Gradys.
There is more seating in general on the 275 with the wider passenger seat that might hold a couple of kids or an adult and a kid and the seat behind the caption's chair. (The Grady had cushions that snap in there on both sides for two seats behind the help seats)
The Grady bridge is a bit higher with 2 steps up from the cockpit instead of one for the Aquasport.
The cabin layouts are similar with the exception of the bunks - it looks like you could sleep 5 in the 275 cabin.
If the choice was up to my wife, she would pick the Aquasport for sure because of more creature comforts like the seating and bunks.
Therefore, I wouldn't show it to my wife and would just buy the Grady... 8)
Cheers,
-Scott