It's a little head-in-the-sand to suggest that restauranteurs and club owners and whoever else are going to be doing these sorts of things "a few times". These people are chefs and bartenders. They aren't Danny Meyer or something. They get one - maybe two - bites at the apple before they're done.
That's why it's useful to consider best case, worst case, best guess scenarios. It's also why different investors can come up with a wide range of valuations when they get down to considering an investment. In my personal experience, few financiers place significant reliance on projected financials - it's the underlying assumptions / notes that matter.
Just because it's difficult to forecast a year out also doesn't mean that it shouldn't or can't be done especially since investors themselves have to assume that they won't be able to exit within a year. Coming up with better projections for ROI just adds more datapoints from the very people/entrepreneurs who should know their space/market best (especially in more stable industries - I note that Wilson emphasizes that this is how he thinks of non-tech businesses).