Prime buying season is late Spring/early Summer when everyone wants to get onto the water. Demand and prices are usually highest then. That is in a normal economy.
Hard to say in this economy. I can tell you that Fall and Winter are traditionally buyer's season. People are wanting to unload boats before winter storage and maintenance and let someone else deal with it. Right now, I'd say year round is a buyer's market. Buyers can afford to walk away and wait. There are lots of boats available out there right now.
If you're willing to hold out on winter storage, sit on it and start offering it for sale in March when the weather starts to get warm. If the boat is well-kept, consider going through a broker as an option. They'll be able to put it in front of buyers. Not a lot of brokers will deal in sub $15K boats due to the low commission for the effort but I know a couple in the Annapolis area who will, for example.
Honestly, decide on your asking and accept price and post it in the Spring on Craigslist and the local boat rag when you're ready. If it is a good, well-kept boat, it will sell. Just price it fairly. Certain things add value (electronics, upgrades, new engine, etc), others don't (cushions, rigging, etc).
Some advice for selling:
* Varnish the wood before selling. People like pretty wood. I oil mine now but when my boat goes on the block, I'll varnish the exterior wood.
* Take all your personal gear off the boat before taking pictures or showing it. People want to imagine their stuff on the boat, not yours. Stuff sailbags and other items like life jackets into lockers or storage space to enhance the openness of the boat.
* Wash the exterior and paint the bilge. Clean, dry bilge is good. Shiny, clean boats equates to nicely kept boat in a potential buyer's eyes.
Lots more things you can do but those are good starting points.
SV South Paw
2000 Hunter 340
South River, MD