Giving someone information or advice is not automatically condescending. It is very much in the manner of presenting and in the tone. Some are better at this than others. I agree that sometimes it is better to let some learn "the hard way" as long as they cannot do serious damage or suffer so much that they are turned off completely.
It depends on the setting, too; I have to operate differently when taking hikers from my hiking group somewhere than I do when taking a friend who thinks they are ready for backpacking. It's much easier to be direct with a friend.
And, there are always people who will be upset with any hint that they are doing something "wrong." So no matter how nicely I have suggested something I someimes get a glare. How dare you suggest that nice fellow at REI was wrong? And of course, the budding gear freak is going to be absolutely in love with his wonderful nice new 4 season ten pound tent! It does everything and anything he wants it to! How could you even hint....
Currently I am reading Allen & Mike's Really Cool Backpacking Book, which is a great short read for a newbie - but I disagree with a number of things they say. Despite that, I wouldn't hesitate to recommend it to newbies because it really introduces them to the process of collecting gear in a humorous and informative way, without loading the newbie down with endless details. The underlying message is that backpacking is a set of skills more than anything else - navigation, site selection, clothing selection, etc. all get a basic but good summary to get them going.
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