Ah, the proverbial question
I will give you my thoughts and suggestions. First, the number of $1,000s will dictate the individual model and potential age. Newer/higher end models tend to be more expensive. Although, it is the end of the season and you should be able to work a deal.
First, I would only buy a 4-stroke PWC. I expect 2-cycle to be banned at some point (other parts of the country are already doing this). In addition, the 4-stroke PWCs are much cleaner, quieter, and reliable than their 2-cycle counterparts. That being said, you are now in the 2002 and later models.
The top industry brands are Sea-Doo, Yamaha, Kawasaki, and Honda.
You now have to decide the application of the PWC. Do you want a 3 person cruiser? Do you want a one person muscle craft?
So, post your application and price range and I can give you a more focused view.
Jetskier