In Principals and Practices of Winemaking, Roger Boulton, Vernon Singleton, Linda Bisson and Ralph Kunkee of UC Davis devote a large part of their opening chapter to the planning and other considerations you need to address before making wine commercially. Some of it consists of lists of questions covering finance and regulatory areas such as: When is an operating profit likely? and When is a return on investment likely? They cover issues pertaining to winery design and operation: Can owning a winery be avoided or delayed by custom crushing? and marketing nightmare scenarios: What can/will be done if wines are judged to be lower quality or are slower to sell than expected?
But they also offer some pretty interesting observations and give their opinions on what they believe make a successful winery operation. Some gems that I have highlighted in my copy:
"Over the last century, the average annual increase in wine production in California wineries has been around 6%, but it has come in boom and bust phases with production sometimes exceeding demand. The financial stress resulting from failure to face reality is especially disheartening when we see it in the wine aficionados whose burning desire is merely to make good wine; but we have also seen financial catastrophes in large-scale, and supposedly sophisticated, corporations"
"In the past 30 years, in California, it has been common for the first two owners of new wineries to fail or get financially overextended before perhaps the third owner begins to profit. Exceptions to this pattern have generally been those who planned more thoroughly and grew carefully with little borrowing. Also, successful winemakers tended to be initially modest-sized, but not too small, with some of their own vineyards."
"It is usually easier to succeed as winery number 50 in a famed district than number one in an unknown area."
Heartening and chilling - all at the same time!

Following Grapes On Their Journey To Wine
Vinography: A Wine Blog provides a handy list of wineries that maintain blogs. See the site for the complete list. Here are a few I’ve pulled for you to peruse at once (over a bold Cab, perhaps): Pinotblogger Mia’s…
[...] In some ways I think Hugh is restating, in a more forceful and thought provoking way, something that Boulton et. all said in Principals And Practices of Winemaking: It is usually easier to succeed as winery number 50 in a famed district than number one in an unknown area. [...]