I appreciate all the help and info you have given. I really want something and it just shakes my nerves on buying something that won't last. I know it's very speculative but is it possible for these boats to last another 10 years? I guess it all depends on use and maintenance and I don't have any idea what this boat has seen in the past. I hate to keep bugging y'all with random questions but I just want to learn all I can and it seems like google is staring to be a dead end.
Personally, I prefer the newer boat (2000) with green interior. That doesn't make it a better boat though, the history of the boat is what counts. Like any boat, these will need maintenance and it's buyer beware so be prepared to replace things as they're needed such as the engines and associated wiring/switches, etc. Compression test and water test are mandatory if you're buying a used "running" boat due to the engine replacement is not priced in.
If you keep the boat for another 10 years I'm fairly confident the carburetors and fuel system will need rework and you will likely replace one or probably both motors at some point but fortunately these remanufacured motors are among the least expensive in the marine industry (shop labor rates still apply though!).
If you know someone who has an ear for the Seadoo 2-stoke engine and is willing/capable of diagnosing/tuning them, then you have a giant head start in the learning curve.
It will make a difference if you're capable of replacing the motors and performing the maintenance yourself, otherwise if you cannot remove and replace a motor then I think something perhaps not so temperamental as a 2-stroke Seadoo might be a better choice.
I can understand the attraction to this boat, and maybe to you based on the experience of your friends running their seadoos you feel comfortable with your abilities and that's fine. Later seadoos are running 4-stroke engines which aren't quite so temperamental as 2-stroke engines but themselves have their own unique set of problems, mainly the factory exhaust valve stems are known for corroding so the valve head pops off and punches a hole in the piston (ruining the engine) The aftermarket exhaust valves and the valves in the later 4-stroke engines address this problem completely. If you wind up with a 4-stroke from this era which hasn't had the cylinder head reworked, I would do that ASAP to avoid having to replace the motor.
They use less fuel too, but they're still jets so they consume more than a comparable stern drive. Maybe you should take a look at the 4-stroke Seadoo boats?
There is a lot to like about the 2-stroke Sportster/Speedster boats IMO and I enjoy mine tremendously, but I'm a mechanic capable of repairing anything that might go wrong so I'm not paying shop rates. I've done plenty of wrenching on mine to bring it back into shape from years of neglect so I think if your friends are well experienced with caring for and tuning/diagnosing 2-stroke Marine engines(esp. Seadoo) then you may be capable of overcoming problems as they occur, these boats really aren't completely trouble free and they require more attention than most boats so expect you will experience a learning curve.
If you just want something you can turn the key and go with a minimum of fussing with, it's difficult to beat a small ski type boat running a 4.3 V6 mercruiser stern drive. They're a bit heavier and more to deal with in terms of trailering and hoisting, etc. than the Seadoo, and a small car certainly cannot pull one down the road safely, there are so many factors you must consider when making your choice it's impossible for me to say which is best for your circumstances.