Although it isn't strictly about effective winery web sites (the focus of this blog and The Winery Web Site Report), this article about J Winery using software to better understand how to sell its wines is a worthwhile read.
Web site or software, it really is all about selling (more/all) of your wine. And it's always interesting to get an inside picture of how one winery is dealing with a problem (lack of good visibility into sales) that affects many wineries. Baseline ("The bottom line in IT") does a good job of dissecting specific information technology projects.
It also obliquely mentions the big technology issue for small-to-medium wineries: systems integration (see my upcoming column in the Harvest Fair issue of NorthBay biz).