As a wannabe regatta photographer I can tell you that it's a damn hard way to make a dollar. Add in a chopper and yeah, the prices are going to be outrageous.
A couple examples from my experience . . . Let me start by saying I'm not a professional photographer; I don't sell much but I don't try to either. I have been told though that my work is as good as, or better than, what's been presented for sale at Whidbey Island Race Week in the past.
Last year 5 of us from the local camera club took pictures at the Emerald Cup Regatta on Fern Ridge Reservoir. Frank, one of the other photographers, provided a bow rider for the photo boat for the 3 day event. I put him up on my boat and the YC provided Frank and I dinner at the Saturday night shindig. After the regatta the photographers each gave me their best images (full res) and I made up 8.5 GB dual layer DVDs. We sold all of 4 at $25 each; that was for over 1,000 images sorted by fleet and we barely made enough to cover Frank's gas for the weekend. Not enough to cover the DVDs or our time. Some of my images can be found here:
http://www.flickr.com/photos/36153401@N08/sets/72157630399134982/
This year we had a great regatta with plenty of wind, a squall coming up behind and hitting as the fleet was completing the run to the leeward mark, and an S20 sinking due to the squall. Lots of action and some fantastic photos. As far as selling the photos goes, we tried a different approach and I brought up an event website at ExposureManager.com. We offered full res downloads, prints of various sizes, mouse pads, t-shirts, coffee cups, etc. at extremely reasonable prices. Being a sailor, I know how cheap we can be, so I set things below the (what I thought were) overly high recommended price points. Big mistake. By the time we paid for the printing and 3 months of website hosting we made less than $50. I'm not convinced that we'd have made any more if I'd left the standard pricing in place - frankly I think we'd have had fewer orders.
Frank (a former sailor/racer btw) has already said that he's not sure he's interested in doing the regatta next year. That means we've got no go-fast boat and, if we do it at all, we'll have to use my boat. Not a huge deal, but it probably means none of the close following shots with the big boats 'cuz I can't keep up with them and I won't crowd the mark to get the shots from a slow boat. And even if we do take pictures I'm not sure we'll make them available for sale. It's just not worth the expense if you don't have the volume to "throw out" 98% of your salable images and still make money.
