I just purchased a boat this Spring in Wisconsin. As I have looked at many online, and I have a good idea on what they are now going for. I made a guesstimate on what I would pay for that boat before I looked at anyone elses replies. I came up with a max of $4500.00. And I would feel comfortable around $4000.00.
And I feel I would have gotten a GREAT deal if I got that boat for anything under $3600.00.
Also, the market of your boat has a lot to do with how much water you have. Here in Wisconsin, with a ton of water for fishing and duck hunting activities. There are a ton of used boats out there. There's no, "I have to have that boat", because another one usually pops up a week later that's always similiar. I tend to find that the best time to sell a boat is at the end of February/early March. Guys will spend more on a boat due to cabin fever, and there are not many boats on craigslist/classifieds etc. Therefore it is a harder time to COMPARE used boats and their prices at that time.
Now that fishing season in Wisconsin has been open for 2 weeks. The craigslists and classifieds are flooded with similiar boats. And to make matters worse, most people have their watercraft situation figured out for the summer. So their is a decreased want/need for a boat right now.
On the other side of the coin, the best time to buy is right now, when the classifieds are overstocked with used boats. Give a guy a low offer, if he doesn't like it, go on to the next boat. The next best time to buy is fall. Right before people need to spend that extra money to winterize and store their boats. Also, their mind set is focused on hunting, so their out looking for that extra cash for that new bow or rifle. With that in mind, a good boat can usually be had for less than market value.
If I were you, I would hold on to it for this year. MAKE SURE YOU USE IT. It is better for a outboard to be used than to sit.
And then I would sell it in February when the fishing/cabin fever is at it's highest.
My .02 cents,
Good Luck.