I agree with most of what has already been said, but on top of that I'd definitely make sure you look over the boat as well as check to make sure there haven't been any claims, losses and so forth with regards to the insurance company. With it being a Florida boat, there's a decent chance that it could've been in any number of hurricanes over the past 20+ years, so I'd make sure that there isn't any obvious damage and then also have a surveyor inspect the boat with you. Below are two links to surveyor sites where you can search for one in your area. With regards to the boat itself, I don't know very much at all about the 265 Express's, so I'd definitely have a surveyor go out with you and look over everything. That being said, 2002 is from what I've heard kind of a transitional year where they started going from 2 stroke motors to 4 stroke motors and making a few changes to the boats to allow for the extra weight. I believe most of them would've had Yamaha HPDI outboards, which are a 2 stroke.
They are from what I've heard extremely reliable, though they will burn some oil, they'll be a little bit louder than a 4 stroke and you'll probably smell some exhaust. If they are 4 stroke Yamaha's around that vintage then also as stated above, make sure the surveyor or a Yamaha tech can drop the lower units and look up at the exhausts on the engines to make sure there isn't any corrosion. If there is, it's about $600-$700 in parts per motor, which can come out to around $1,500-$2,000 per motor to have the exhausts done. Which you don't want to spend top dollar on the boat to then have to spend potentially another $4k right away fixing the motors, if there is an issue, and you could work that into the price if they do need to be repaired. With regards to the boats age, I just bought my 2004 GW 228 Seafarer almost a year and a half ago and it was in fantastic shape. So it's not necessarily just an "age" thing, but more often than not it's about how the previous owners of the boat treated it or maintained it, or if it was neglected. Lastly, as mentioned above, a 265 Express is definitely a bigger boat for a newer boater, and there are similar boats like a 232 Gulfstream that also might work out well for you, especially if you're only going to use it a few times a month. I think a little bit more information about yourself like your budget and intended usage of the boat will help out some as well. Good luck!
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