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I guess it depends what one uses it for. But I have been very happy with my 16GB ipad 2, although like others, I don't store a lot of content on it. mainly space is taken up when I load videos on to watch when travelling.
 
16gb iPad 1. I have about 9gb free. Music comes from iTunes Match, so I have access to about 50gb of music there that can be streamed to the iPad. If I want a movie or two I can fit them in and then delete them when I'm done, although I rarely do it. Most movies come from Netflix streaming or streaming from my home DVR via Vulkano (a Slingbox alternative).

I have no worries about the 16gb new iPad that's on the way to me.
 
I wish I could say the same but I do regret my 16GB pre-order (being held for pick up at FedEx tomorrow).

I will probably hunt down a 32GB one tomorrow, if I can find one...
 
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