I imagine the spring and summer would be the "peak" season for selling and is going to likely be the time of year where the seller will get the most money for selling their boat. That being said, it really just depends on where you live and where you're buying the boat from, if they have "seasons" and so forth. Up here in the Seattle/PNW area, the peak season is spring/summer and then boating almost comes to a standstill in October/November when it turns to winter, the weather gets worse and fishing ends. I imagine other parts of the country are similar, but considering you're looking in southern Florida, I imagine you must have boating/fishing almost year round, which I imagine won't drop prices down considerably or anything. I personally bought my boat back in Maryland in October of 2021, which seemed like it was the tail end of the season and like the GW dealership that I bought it from was trying to sell it off before the winter. If possible and you can shop around, winters up here or elsewhere are typically the best time to buy and will get you better prices as opposed to being in the peak season. In regard to ages of boats, I've got a 2004 GW 228 Seafarer that's just over 21 years old now and she's still going strong, knock on wood. I always recommend that everyone pay to have a surveyor inspect the boat for them before purchasing so that you don't get any surprises. But as long as the boat checks out, I don't see any issue with a 20 year old boat, or those that are even older than that. I will say though, if you do plan on financing a boat, a lot of banks and/or credit unions won't loan on anything more than 20-25 years old. So, that might be something to consider if you plan on going that route.