I tried a number of cities, your own home of San Francisco, my own of Cambridge, UK as well as some others I'm familiar with like Bangalore and Tapei. I was very disappointed that the San Francisco guide was of far worse quality than the Cambridge guide for example. I would have expected since the company is there, you might have something interesting to say about the city. Apparently not.
The list of events is worse than useless, it's cheap and tacky. For example, the events for Bangalore lists events in places such as Shanghai and somewhere on the Indian coast over 500Km away, as well as events tourists couldn't possibly be interested in such as agricultural machinery expos. You just can't do this sort of thing by pulling events unfiltered from external sources, that just doesn't work. Full stop. I want a sensible listing of events that I can filter by my interests, each one with a map of the location and public transport details.
The issues you have can't be fixed with copy editing. You simply can't produce a guide to a place you've never been, and you really shouldn't try. This talk about covering a "long tail" of destinations depresses me. Leave that stuff to wikitravel, you should be producing a polished commercial product. At a minimum you need to at least have had one person representing the company visiting each place you produce a guide to. You aren't in the business producing a general purpose guide, you're in the business of knowing everything there is to know about a city and giving people a decent interface to filtering it. Quite frankly, I don't see how you can do that without a team of people going to a place for at least a month.
Some features I'd pay for:
* Suggested itineraries for days, based on a database of places and activities filtered by my interests and biased by predicted weather.
* Some sort of more/less detail slider for each page enabling me to customise the text.
* Complete and up to date public transport listings for the destination, cross referenced with the events and places I've chosen to add to my guide.
Above all, if I'm paying for something that costs about the same as the rough guide I want something at least as good quality as the rough guide. You aren't going to get that with wikitravel and creative commons photos.