my advice...
...based on very recent experience, is that it pays to have a large number of very well composed pictures in your ad. I placed an ad on this site in April with no pictures, and got very little interest. I also ran the same ad for 2 months last fall, with only a couple of nibbles. In late June, when the ad expired, I paid extra (not much extra) to put 7 pictures with the old ad. Within a week, I have had 4 inquiries, and I just sold the boat.My take on this is that buying any sailboat is an irrational act. You would think that anyone seriously in the market would look at most of the boats in the nearby area which met their requirements. But this appears not to be the case. Good pictures get people worked up, and motivate them to get out and do the irrational thing of actually buying.I'd take a lot of trouble with the pictures, making sure you clean up the boat, and taking lots of shots so that you get the exposure and focus right. I ended up taking shots on 4 different days, because I wasn't happy with some of them. (Mostly exposure problems.) It's amazing how many ads you see on yachtworld.com with tons of pictures in which the boat is cluttered with junk, spray bottles, etc. It seems worth the effort to present a nice picture, given that you're selling a dream more than a boat. As far as time of year, I think this is still fine. Maybe by late September, it's getting slow, as obviously people don't want to buy and then store the boat right away for the winter. It's probably obvious to you, but it also seems to just take a while sometimes. Like maybe a year or more for a bigger boat. Also pricing realistically, etc. Good luck!