Above all else you need to assure yourself that the boat is watertight. The best way to do this is on the water - it would be very difficult to be certain just by looking at the boat because tiny cracks or holes in the hull can cause a lot of water to get in if underwater. Cracks are most likely in the area of the drivewell, the scupper holes and the seat pegs; the rest of the boat is pretty resilient but still check, double check & make sure there is no obvious piercing or deep cuts. If you uncover that the owner has "mended" a crack you should walk away.
I am assuming that it will have the cam-lock system for locking the drive in place in whch case you need to look carefully inside the boat at the cam columns one either side of the drive well - these are the plastic columns into which the cam bolts (which hold the drive in place) are screwed. If there is any sign that the cam columns are cracked or have been tampered with (e.g. evidence of "fixing up") I recommend that you walk away.
Owners were offered a retro-fit kit to reinforce the drivewell on some Adventures around this time - you can search on this site to find info about which serial numbers were included - then you can check your boat prior to purchase to find out whether or not it qualified for the kit (the serial number is scratched into a panel on the outside of the stern of the boat - rub some talc or similar over the panel to be able to read the characters more easily ). The kit included a fibreglass "nose" and longer cambolts. The "Nose" was stuck inside the boat to reinforce the forward end of the drivewell (if installed it should be obvious when you look inside the front hatch at the inside front end of the drivewell). You would need to ask about the longer cambolts to find out if the owner replaced them. If the boat was eligible and the kit wasn't installed I am pretty sure that you would be able to get the kit from Hobie. Hobie offered an extended warranty if the kit was installed but I guess this boat would still be out of even that warranty period by now.
Have a look at the rudder - you may find the standard issue but maybe the owner has upgraded to the larger rudder which is much better suited to the boat.
Check the boat for non-standard upgrades which have involved drilling holes in the hull - owners frequently pimp their rides - any such mods may have been done well or badly, you will need to check, but either way they are likely to negatively affect resale value.
If you are getting a 2-piece paddle with the boat check it still comes apart (they sieze up if sand gets into the joint - I bought a 2nd-hand Adventure some years ago without checking the paddle and to this day the 2-piece is a 1-piece).
The drive is important - they are pretty robust (one of mine is still going like the day I first got it after several hard years of use) and repairable, though. A good look at the drive may give an indication of how well used and maintained the boat (and drive) have been - sloppy is one thing, but full of sand and badly corroded by not being washed down after saltwater use is another (though as I say, you should be able to repair, replace, readjust easily enough). Does it have the original pointed fins or the (more desirable) square tops (ST) or longer ST Turbo fins? Are the pedals in good order (they do wear out - though spares can be bought).
This is about as much as I can think of just now - others may be able to add more.
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