$1000 is a down payment not a deposit. $50 is too cheap. $100-200 seems right, after all you winterized it and put it away. Going through all that work is time, money and effort.
One of you mentioned that they are even more undecided after they go for a ride on an unfamiliar boat. Although the word "empathy" wasn't said, it was implied. Not only are you parting with $7500, you're also taking on a headache if things go wrong. Just because I like the boat now in December doesn't mean I may like it later, and how can I be so sure that the boat wont have problems? Im sure boat is well maintained, but the fact is its 20 years old. What if the hull cracks? The interior is rotten? Engine problems? These are all things I've witnessed before on our family's boat. Losing $7500 is bad but being reminded of it every day is worse. I once bought a leather jacket for $300. I thought it was the style i liked. It looked ok and everything, but sure enough a week later I didnt like shinier leather, it felt a little small, and it wasnt EXACTLY what I wanted and sure enough I couldnt stand to look at it so I threw it away. Further, my family buys used cars and we've usually done very well, sure enough our confidence in our ability to buy and not looking hard at the car caused us to buy it. A week later no one liked driving the car, simply because we knew we'd been had.
Generally I research the hell out of anything expensive I buy. If I haven't researched it then I'm just as shifty as these potential buyers, even after an anologous "test ride." I dont buy something unless I'm comfortable with buying it or am willing to deal with the financial repercussions if everything falls apart.
When there was an Elite for sale last year for $350 I passed because the description was short. I figured, how can a ski thats normaly priced $900 be so cheap? Something must be wrong. Sure enough someone here said it was skidawgs old ski and could vouch for it. I lost out on my chance.
Here's a tip from left field: Don't trade a boat for money. Trade your personalities in the process. Spend plenty of time conversing. Trade WHY you ski. Trade WHY you are selling this boat and trade WHY you bought it in the first place. Explain the why the wake is the shape it is. If its not up to snuff with modern boats big deal, its from 93, compare it to boats at the time. If this guy and his girl are skiing in the winter then the must be serious, or they just want a christmas pull. Make the guy comfortable with trading his money for your boat with you and that should iron out any indecision.
Watch all of this.
http://www.youtube.com/watch?v=l5Tw0PGcyN0